(1S,2S,6R)-(+)-(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetic acid | 104640-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,6R)-(+)-(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetic acid
• 英文别名: (1S,2S,6R)-2-(2-hydroxy-2,6-dimethyl-6-vinylcyclohexanyl)acetic acid；(-)-anastrephin γ-hydroxy acid；2-[(1S,2R,6S)-2-ethenyl-6-hydroxy-2,6-dimethylcyclohexyl]acetic acid
• CAS: 104640-77-9
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: MKKFTMMPINDCQH-DLOVCJGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R)-(+)-(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetic acid 在 重氮甲烷 作用下， 以 甲醇 为溶剂， 以100%的产率得到C₁₃H₂₂O₃
  参考文献：
  名称：

  Glucosylated Suspensosides, Water-Soluble Pheromone Conjugates from the Oral Secretions of Male Anastrepha suspensa

  摘要：

  A diastereomeric mixture of the glycosylated pheromones (6R)- (1a) and (6S)-beta-D-glucopyranosyl 2-(2,6-dimethyl-6-vinylcyclohex-1-enyl)acetate (1b), which we named respectively suspensoside A and suspensoside B. was isolated from the oral secretions of male Caribbean fruit flies, Anastrepha suspensa. The absolute stereochemical configurations were established using microsample NMR instrumentation, chiral gas chromatography, and chemical synthesis utilizing pure enantiomers of anastrephin, (3aS,4R,7aS)- (4a) or (3aR,4S,7aR)-4,7a-dimethyl-4-vinylhexahydrobenzofuran-2(3H)one (4b), its the aglycon precursor.

  DOI：

  10.1021/np800096k
• 作为产物：
  描述：

  (E,E)-3,7-Dimethyl-9-(tetrahydropyran-2'-yloxy)-2,7-nonadien-1-ol 在 2-羟基吡啶 、 氢氧化钾 、 sodium hydroxide 、 正丁基锂 、 三苯基甲烷 、 三氟化硼乙醚 、 sodium 、 4-甲基苯磺酸吡啶 、 汞 、 lithium bromide 作用下， 以 甲醇 、 六甲基磷酰三胺 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.6h， 生成 (1S,2S,6R)-(+)-(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetic acid
  参考文献：
  名称：

  Mori, Kenji; Nakazono, Yutaka, Liebigs Annalen der Chemie, 1988, p. 167 - 174

  摘要：

  DOI：

文献信息

• Diastereoselective Synthesis of (±)-Epianastrephin, (±)-Anastrephin and Analogs Thereof
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US20170305874A1

  公开（公告）日：2017-10-26

  A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R 1 is ethenyl, R 2 and R 3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R 2 is ethenyl, R 1 and R 3 is methyl and n is 1), and analogs thereof (wherein: R 1 is H, C 1-5 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, R 2 is H, C 1-5 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, R 1 and R 2 together with the carbon atom they are attached form a C 3-6 cycloalkyl ring, R 3 is C 1-5 alkyl and n is 0-2):

  从具有化学式（I）的取代环状酮合成具有化学式（IV）的反式γ-内酯的过程。对（±）-epianastrephin（1）进行立体选择合成（其中：R1为乙烯基，R2和R3为甲基，n为1），（±）-anastrephin（2）进行立体选择合成（其中：R2为乙烯基，R1和R3为甲基，n为1），以及它们的类似物（其中：R1为H，C1-5烷基，C2-6烯基或C2-6炔基，R2为H，C1-5烷基，C2-6烯基或C2-6炔基，R1和R2与它们附着的碳原子一起形成C3-6环烷基环，R3为C1-5烷基，n为0-2）。
• Compositions and methods for attracting Anastrepha species
  申请人：The United States of America as represented by the Secretary of Agriculture

  公开号：US08128948B1

  公开（公告）日：2012-03-06

  A composition containing suspensolide and optionally at least one of γ-hydroxy acid of epianastrephin, γ-hydroxy acid of anastrephin, 2,6-dimethyl-6-vinyl-cyclohexeneacetic acid, β-D-glucopyranosyl 2,6-dimethyl-6-vinyl-cyclohex-1-ene-1-acetoate, or mixtures thereof, and optionally a carrier or carrier material; the composition contains no β-bisabolene and no α-farnesene. A method for attracting Anastrepha species (e.g., A. suspensa) involving treating an object or area with an Anastrepha species attracting effective amount of the above composition.

  一种含有悬浮酮和至少一种γ-羟基酸的复合物，该γ-羟基酸可以是epianastrephin的γ-羟基酸，anastrephin的γ-羟基酸，2,6-二甲基-6-乙烯基-环己烯乙酸，β-D-葡萄糖吡喃基2,6-二甲基-6-乙烯基-环己-1-烯-1-乙酸酯，或其混合物，并且可以含有载体或载体材料；该组合物不含β-百里香烯和α-法尼烯。一种用上述组合物的Anastrepha物种（例如，A. suspensa）吸引有效量处理物体或区域的方法。
• Diastereoselective synthesis of (±)-epianastrephin, (±)-anastrephin and analogs thereof
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US10011580B2

  公开（公告）日：2018-07-03

  A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R1 is ethenyl, R2 and R3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R2 is ethenyl, R1 and R3 is methyl and n is 1), and analogs thereof (wherein: R1 is H, C1-5 alkyl, C2-6 alkenyl or C2-6 alkynyl, R2 is H, C1-5 alkyl, C2-6 alkenyl or C2-6 alkynyl, R1 and R2 together with the carbon atom they are attached form a C3-6 cycloalkyl ring, R3 is C1-5 alkyl and n is 0-2):

  一种从具有式(I)的取代环酮合成具有式(IV)的反式融合γ-内酯的工艺。一种非对映选择性合成(±)-epianastrephin (1)（其中：R1 是乙烯基，R2 和 R3 是甲基，n 是 1）、(±)-anastrephin (2)（其中：R2 是乙烯基，R1 和 R3 是甲基，n 是 1）及其类似物（其中：R1为H、C1-5烷基、C2-6烯基或C2-6炔基，R2为H、C1-5烷基、C2-6烯基或C2-6炔基，R1和R2与它们所连接的碳原子一起形成一个C3-6环烷基环，R3为C1-5烷基，n为0-2）：
• Resolution and assignment of absolute configuration to the enantiomers of anastrephin and epianastrephin and their analogs
  作者：Lucjan Strekowski、Melean Visnick、Merle A. Battiste

  DOI：10.1021/jo00375a016

  日期：1986.12
• MORI, KENJI;NAKAZONO, YUTAKA, LIEBIGS ANN. CHEM.,(1988) N 2, 167-174
  作者：MORI, KENJI、NAKAZONO, YUTAKA

  DOI：——

  日期：——