(1S,13S,14S,15S,20R,21R,22R)-14,20-DIHYDROXY-13,15,21-TRIMETHYL-22-(1-methylpenta-2,4-dienyl)-oxacyclodocosa-11,16-dien-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1S,13S,14S,15S,20R,21R,22R)-14,20-DIHYDROXY-13,15,21-TRIMETHYL-22-(1-methylpenta-2,4-dienyl)-oxacyclodocosa-11,16-dien-2-one
• 英文别名: (11Z,13S,14S,15S,16Z,20R,21S,22S)-22-[(2S,3Z)-hexa-3,5-dien-2-yl]-14,20-dihydroxy-13,15,21-trimethyl-1-oxacyclodocosa-11,16-dien-2-one
• 化学式: C₃₀H₅₀O₄
• 分子量: 474.725
• InChiKey: UPQFDHFDYFIFJY-ZXGACEKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,10-癸二醇 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 氟化氢吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 吡啶 为溶剂， 生成 (1S,13S,14S,15S,20R,21R,22R)-14,20-DIHYDROXY-13,15,21-TRIMETHYL-22-(1-methylpenta-2,4-dienyl)-oxacyclodocosa-11,16-dien-2-one
  参考文献：
  名称：

  Discodermolide / Dictyostatin杂种：合成和生物学评估。

  摘要：

  [结构：见正文]已设计并合成了二编码器莫迪尔和双香豆素（3，26）的两个杂合类似物。这些是第一个discodermolide的大环类似物，并对其生物学活性进行了评估，并与线性discodermolide的类似物进行了比较。

  DOI：

  10.1021/ol026942l

文献信息

• [EN] ANALOGS OF DISCODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF<br/>[FR] ANALOGUES DE DISCODERMOLIDE ET DE DICTYOSTATINE-1, INTERMEDIAIRES CORRESPONDANTS, ET PROCEDES DE SYNTHESE CORRESPONDANTS
  申请人：UNIV PITTSBURGH

  公开号：WO2004022552A1

  公开（公告）日：2004-03-18

  A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, -RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or -NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, -CH2CH(CH3)-, -CH=CH-, -CH=C(CH3)-, or -C=-C-; R4 is (CH2)p where p is an integer in the range of 4 to 12, -(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs I)CH(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-, -(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-, wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1, Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.

  以下是该结构的化合物：其中R1为H、烷基基团、芳基、烯基基团、炔基基团或卤素原子；R2为H、烷基基团、芳基、苄基、三苄基、-SiRaRbRc、CH2ORd或CORe；Ra、Rb和Rc独立地为烷基基团或芳基；Rd为烷基基团、芳基、烷氧基烷基团、-RiSiRaRbRc或苄基，其中Ri为烷基烷基团；Re为烷基基团、烯丙基基团、苄基、芳基、烷氧基或-NRgRh，其中Rg和Rh独立地为H、烷基基团或芳基；R3为(CH2)n，其中n为0到5范围内的整数，-CH2CH(CH3)-、-CH=CH-、-CH=C(CH3)-或-C=-C-；R4为(CH2)p，其中p为4到12范围内的整数，-(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-、-(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs I)CH(Rs2)C(Rs3)=C(Rs4)-、-(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-、-(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-，其中y1和y2为1，y3、y4和y5独立地为0或1，Rk1、Rk2、Rk3、Rk4和Rk5独立地为H、CH3或OR2a，Rs1、Rs2、Rs3和Rs4独立地为H或CH3，其中R2a为H、烷基基团、芳基、苄基、三苄基、-SiRaRbRc、CH2ORd或CORe；R5为H或OR2b，其中R2b为H、烷基基团、芳基、芳基、苄基、三苄基、-SiRaRbRc、CH2ORd或CORe；前提是该化合物不是dictyostatin 1。
• ANALOGS OF DICODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF
  申请人：CURRAN DENNIS P.

  公开号：US20090036691A1

  公开（公告）日：2009-02-05

  A compound of the following structure: wherein R 1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R 2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; R a , R b and R c are independently an alkyl group or an aryl group; R d is an alkyl group, an aryl group, an alkoxylalkyl group, —R i SiR a R b R c or a benzyl group, wherein R i is an alkylene group; R e is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or —NR g R h , wherein R g and R h are independently H, an alkyl group or an aryl group; R 3 is (CH 2 ) n where n is and integer in the range of 0 to 5, —CH 2 CH(CH 3 )—, —CH═CH—, —CH═C(CH 3 )—, or —C≡C—; R 4 , wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, R k1 , R k2 , R k3 , R k4 and R k5 are independently H, CH 3 , or OR 2a , and R s1 , R s2 , R s3 , and R s4 are independently H or CH 3 , wherein R 2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e ; and R 5 is H or OR 2b , wherein R 2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, —SiR a R b R c , CH 2 OR d , or COR e .

  以下为结构式的化合物： 其中R1为H、烷基、芳基、烯基、炔基或卤素原子； R2为H、烷基、芳基、苯甲基、三苯甲基、—SiRaRbRc、CH2ORd或CORe； Ra、Rb和Rc独立地为烷基或芳基； Rd为烷基、芳基、烷氧基烷基、—RiSiRaRbRc或苯甲基，其中Ri为烷基； Re为烷基、烯丙基、苯甲基、芳基、烷氧基或—NRgRh，其中Rg和Rh独立地为H、烷基或芳基； R3为(CH2)n，其中n为0至5的整数，—CH2CH(CH3)—、—CH═CH—、—CH═C(CH3)—或—C≡C—； R4为H或OR2b，其中y1和y2为1，y3、y4和y5独立地为0或1，Rk1、Rk2、Rk3、Rk4和Rk5独立地为H、CH3或OR2a，而Rs1、Rs2、Rs3和Rs4独立地为H或CH3，其中R2a为H、烷基、芳基、苯甲基、三苯甲基、—SiRaRbRc、CH2ORd或CORe；而R2b为H、烷基、芳基、苯甲基、三苯甲基、—SiRaRbRc、CH2ORd或CORe。
• US7968736B2
  申请人：——

  公开号：US7968736B2

  公开（公告）日：2011-06-28
• Discodermolide/Dictyostatin Hybrids:  Synthesis and Biological Evaluation
  作者：Youseung Shin、Nakyen Choy、Raghavan Balachandran、Charitha Madiraju、Billy W. Day、Dennis P. Curran

  DOI：10.1021/ol026942l

  日期：2002.12.1

  [structure: see text] Two hybrid analogues of discodermolide and dictyostatin (3, 26) have been designed and synthesized. These are the first macrocyclic analogues of discodermolide and biological activities were evaluated and compared with linear discodermolide analogues.

  [结构：见正文]已设计并合成了二编码器莫迪尔和双香豆素（3，26）的两个杂合类似物。这些是第一个discodermolide的大环类似物，并对其生物学活性进行了评估，并与线性discodermolide的类似物进行了比较。