1'.2'-Dihydroxy-3'-methyl-3.4-benzotropolon | 22208-89-5

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 1'.2'-Dihydroxy-3'-methyl-3.4-benzotropolon
• 英文别名: 3,4,6-trihydroxy-2-methylbenzo[7]annulen-5-one
• CAS: 22208-89-5
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: XVNQJAJMTXRKQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1'.2'-Dihydroxy-3'-methyl-3.4-benzotropolon 在 sodium hydroxide 、 双氧水 作用下， 生成 2-methyl-2,4-hexadienedioic acid
  参考文献：
  名称：

  1'，2'-二羟基-3,4-苯并呋喃酮的碱性过氧化物氧化

  摘要：

  1'，2'-二羟基-3,4-苯并呋喃酮的碱性过氧化物氧化反应通过相应的1'，2'-醌阴离子进行，该阴离子经历两种类型的过氧化物分解。（a）在低温和碱浓度下，过氧化物主要侵害环己二烯环的3'-和4'-位，并导致形成不稳定的氢过氧化物，其分解为羟基醌，这也直接通过溶剂分解而形成。3'-位的更高反应性归因于其与醌型和托酚酮羰基的共轭。由3'-取代的底物形成的2'-羟基-1'，4'-醌被进一步氧化为托酚酮-3,4-二羧酸酐。（b）在高温和碱浓度下会形成粘康酸通过过氧化氢引起的四羟基苯并呋喃酮和二羟基-2'，6'-醌类酮类化合物对tro环酮环的5位，6位和7位进行攻击。当底物在6-位带有羧基时，不会形成这些四羟基苯甲酮（也可通过水解1'，2'-醌的异常Thiele五乙酸酯获得）；在这种情况下，过氧化物对环己二烯环的1'-和2'-位的侵蚀占主导地位。

  DOI：

  10.1039/j39690000612

文献信息

• EP2296760B1
  申请人：——

  公开号：EP2296760B1

  公开（公告）日：2016-03-16
• USE OF BENZOTROPOLONE DERIVATIVES AS UV ABSORBERS AND ANTIOXIDANTS AND THEIR USE IN SUNSCREENS AND/OR COSMETIC COMPOSITIONS
  申请人：Wagner Barbara

  公开号：US20110123468A1

  公开（公告）日：2011-05-26

  Described is the use of benzotropolone and their derivatives, especially the compounds of formula (1); wherein R 2 , R 3 , R 4 , R 5 and R 6 independently of one another are hydrogen; OH; C 1 -C 30 alkyl, C 2 -C 30 al-kenyl, C 1 -C 30 alkoxy, C 3 -C 12 cycloalkyl or C 1 C 30 hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, CN, or —CO—R 17 ; C 1 -C 30 mono- or dialkylamino; COR 9 ; COOR 9 ; CONR 9 R 10 ; CN; SO 2 R 9 ; OCOOR 9 ; OCOR 9 ; NHCOOR 9 ; NR 9 COR 10 ; NH 2 ; *—(CO)—NH—(CH 2 ) n1 —(PO)—(OR 11 ) 2 ; —(CO)—O—(CH 2 ) n1 —(PO)—(OR 11 ) 2 ; sulphate; sulphonate; phosphate; phosphonate; —(CH 2 ) n2 —[O—(SO 2 )] n3 —OR 11 ; —O—(CH 2 ) n4 (CO) n5 —R 11 ; —(O) n6 —(CH 2 ) n7 —(PO)—(OR 9 ) 2 ; —(O) n6 —(CH 2 ) n7 —SO 2 —OR 9 ; halogen; organosilanyl; organo-siloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 ) n —(X 1 ) 1 or 0 -benzotropolone system, wherein n=1-10 and X 1 =—O—; —(CO)—; —O—CO—; —COO—, —NH—; —S—; —SO 2 —); R 1 , R 7 and R 8 independently of one another are hydrogen; C 1 C 12 alkyl or C 3 -C 12 -cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, or COOR 9 ; COR 9 ; CONR 9 R 10 ; SO 3 R 9 ; SO 2 R 9 ; PO 3 (R 9 ) 2 ; PO 2 (R 9 ) 2 ; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 ) n —(X 2 ) 1 or 0 —*, wherein n=1-10 and X 2 =—C(═O)—; —O—CO—*); R 9 and R 10 independently from each other are hydrogen; C 1 C 18 alkyl or C 3 -C 12 -cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C 6 -C 20 aryl, which may be substituted by one or more G; C 4 -C 20 heteroaryl, which may be substituted by one or more G; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 ) n —*, wherein n=1-10); or R 9 and R 10 together form a five or six membered ring, R 11 is hydrogen; or C 1 -C 5 alkyl; n 1 , n 2 , n 4 and n 7 independently from each other are a number from 1 to 5; n 3 , n 5 and n 6 independently from each other are a 0; or 1; D is —CO—; —COO—; —S—; —SO—; —SO2-; —O—; —NR 14 —; —S 1 R 19 R 20 —; —POR 11 —; —CR 12 ═CR 13 —; or —C≡C—; and E is —OR 18 ; —SR 18 ; —NR 14 R 15 ; —NR 14 COR 15 ; —COR 17 ; —COOR 16 ; —CONR 14 R 15 ; —CN; halogen; Or SO 3 R 18 ; SO 2 R 18 ; PO 3 (R 18 ) 2 ; PO 2 (R 18 ) 2 ; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH 2 )n-(X 1 ) 1 or 0 —*, wherein n=1-10 and X1=—O—; —C(═O)—; —O—CO—; —COO—; —NH—; —S—; —SO 2 —); G is E; C 1 -C 18 alkyl, which is optionally interrupted by D; C 1 -C 18 perfluoroalkyl; C 1 -C 18 alkoxy, which is optionally substituted by E and/or interrupted by D; wherein R 12 , R 13 , R 14 and R 15 independently of each other are hydrogen; C 6 -C 18 aryl which is optionally substituted by OH, C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 1 -C 18 alkyl, which is optionally interrupted by —O—; or Ri4 and Ri5 together form a five or six membered ring, Ri6 is hydrogen; C6-Ci8aryl which is optionally substituted by OH, C 1 -C 18 alkyl or d-C 18 alkoxy; C 1 -C 18 alkyl which is optionally interrupted by —O—; R 17 is H; C 6 -C 18 aryl which is optionally substituted by OH, C 1 -C 18 alkyl or C 1 -C 18 alkoxy; or d-C 18 alkyl which is optionally interrupted by —O—; R 18 is hydrogen; C 6 -C 18 aryl, which is optionally substituted by OH, C 1 -C 18 alkyl or d-C 18 alkoxy; C 1 -C 18 alkyl, which is optionally interrupted by —O—; R 19 and R 20 independently of each other are hydrogen; C 1 -C 18 alkyl; C 6 -C 18 aryl which is optionally substituted by C 1 -C 18 alkyl; and R 21 is C 1 -C 18 alkyl; or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl; * means, that this radical is directed to the benzotropolone moiety; for the protection of human and animal hair and skin against UV radiation.
• US9707417B2
  申请人：——

  公开号：US9707417B2

  公开（公告）日：2017-07-18
• [EN] USE OF BENZOTROPOLONE DERIVATIVES AS UV ABSORBERS AND ANTIOXIDANTS AND THEIR USE IN SUNSCREENS AND/OR COSMETIC COMPOSITIONS<br/>[FR] UTILISATION DE DÉRIVÉS DE BENZOTROPOLONE EN TANT QU'ABSORBEURS UV ET ANTIOXYDANTS, ET LEUR UTILISATION DANS DES ÉCRANS SOLAIRES ET/OU DES COMPOSITIONS COSMÉTIQUES
  申请人：BASF SE

  公开号：WO2009156324A2

  公开（公告）日：2009-12-30

  Described is the use of benzotropolone and their derivatives, especially the compounds of formula (1); wherein R2, R3, R4, R5 and R6 independently of one another are hydrogen; OH; C1-C30alkyl, C2-C30al- kenyl, C1-C30alkoxy, C3-C12cycloalkyl or C1C30hydroxyalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C6-C20aryl, which may be substitu¬ ted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G, C2- C18alkenyl, C2-C18alkynyl, C7-C25aralkyl, CN, or -CO-R17; C1-C30mono- or dialkylamino; COR9; COOR9; CONR9R10; CN; SO2R9; OCOOR9; OCOR9; NHCOOR9; NR9COR10; NH2; *-(CO)-NH-(CH2)n1-(PO)-(OR11)2; -(CO)-O-(CH2)n1-(PO)-(OR11)2; sulphate; sulphonate; phosphate; phosphonate; -(CH2)n2-[O-(SO2)]n3-OR11; -O-(CH2)n4(CO)n5-R11; -(O)n6-(CH2)n7-(PO)-(OR9)2; -(O)n6-(CH2)n7-SO2-OR9; halogen; organosilanyl; organo- siloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar- (CH2)n-(X1)1 or 0 -benzotropolone system, wherein n = 1 -10 and X1 = -0-; -(CO)-; -0-C0-; -COO-, -NH-; -S-; -SO2-); R1, R7 and R8 independently of one another are hydrogen; C1C12alkyl or C3-C12-cycloalkyl, which may be substituted by one or more E and/or interrupted by one or more D; C6- C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G, C2-C18alkenyl, C2-C18alkynyl, C7-C25aralkyl, or COOR9; COR9; CONR9R10; SO3R9; SO2R9; PO3(R9)2; PO2(R9)2; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen to the benzotropolone system or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar-(CH2)n-(X2)1 or 0-*, wherein n = 1 -10 and X2 = -C(=0)-; -0-C0-*); R9 and R10 independently from each other are hydrogen; C1C18alkyl or C3-C12-cycloalkyl which may be substituted by one or more E and/or interrupted by one or more D; C6- C20aryl, which may be substituted by one or more G; C4-C20heteroaryl, which may be substituted by one or more G; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar- (CH2)n-*, wherein n = 1 -10); or R9 and R10 together form a five or six membered ring, R11 is hydrogen; or C1-C5alkyl; n1, n2, n4 and n7 independently from each other are a number from 1 to 5; n3, n5 and n6 independently from each other are a 0; or 1; D is -CO-; -COO-; -S-; -SO-; -SO2-; -O-; -NR14-; -S1R19R20-; -POR11-; -CR12=CR13-; or -C≡C-; and E is -0R18; -SR18; -NR14R15; -NR14COR15; -C0R17; -COOR16; -CONR14R15; -CN; halogen; Or SO3R18; SO2R18; PO3(R18)2; PO2(R18)2; organosilanyl; organosiloxanyl; or a sugar residue linked directly in an α- or β-mode via the anomeric oxygen or via a linear or branched alkylene, alkenylene, alkadiene or alkatriene spacer (sugar- (CH2)n-(X1)1or 0-*, wherein n = 1 -10 and X1 = -0-; -C(=0)-; -0-C0-; -COO-; -NH-; -S-; -SO2-); G is E; C1-C18alkyl, which is optionally interrupted by D; C1-C18perfluoroalkyl; C1-C18alkoxy, which is optionally substituted by E and/or interrupted by D; wherein R12, R13, R14 and R15 independently of each other are hydrogen; C6-C18aryl which is optionally substituted by OH, C1-C18alkyl or C1-C18alkoxy; C1-C18alkyl, which is optionally interrupted by -O-; or Ri4 and Ri5 together form a five or six membered ring, Ri6 is hydrogen; C6-Ci8aryl which is optionally substituted by OH, C1-C18alkyl or d- C18alkoxy; C1-C18alkyl which is optionally interrupted by -O-; R17 is H; C6-C18aryl which is optionally substituted by OH, C1-C18alkyl or C1-C18alkoxy; or d- C18alkyl which is optionally interrupted by -O-; R18 is hydrogen; C6-C18aryl, which is optionally substituted by OH, C1-C18alkyl or d- C18alkoxy; C1-C18alkyl, which is optionally interrupted by -O-; R19 and R20 independently of each other are hydrogen; C1-C18alkyl; C6-C18aryl which is optionally substituted by C1-C18alkyl; and R21 is C1-C18alkyl; or C6-C18aryl, which is substituted by C1-C18alkyl; * means, that this radical is directed to the benzotropolone moiety; for the protection of human and animal hair and skin against UV radiation.
• [EN] BENZOTROPOLONE DERIVATIVES AS ANTIMICROBIAL AGENTS<br/>[FR] DÉRIVÉS DE BENZOTROPOLONE À TITRE D'AGENTS ANTIMICROBIENS
  申请人：BASF SE

  公开号：WO2011048011A2

  公开（公告）日：2011-04-28

  Disclosed is the use of benzotropolone derivatives of Formula (1) as antimicrobial and/or preserving agents.