(E)-3,7-dimethyl-2-octene-1,8-diol | 104266-22-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3,7-dimethyl-2-octene-1,8-diol
• 英文别名: (e,s)-3,7-Dimethyl-2-octene-1,8-diol；(E,7S)-3,7-dimethyloct-2-ene-1,8-diol
• CAS: 104266-22-0
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: ODQHVONZJQWKCN-ZKXNXJMVSA-N

物化性质

• 沸点：
  275.6±28.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3,7-dimethyl-2-octene-1,8-diol 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以80%的产率得到(S,E)-3,7-dimethyl-2-octene-1,8-dioic acid
  参考文献：
  名称：

  Asymmetric synthesis of (E)- and (Z)-3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid

  摘要：

  Both enantiomers and regioisomers of (E)- and (Z)-3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid, which have important biological activity were synthesized by enzymatic transesterification of primary alcohols (E)- and (Z)-10. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.032
• 作为产物：
  描述：

  (E)-6-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid ethyl ester 在 咪唑 、 lithium aluminium tetrahydride 、 pseudomonas fluorescens lipase 、 氰化钠 、 水 、 碘 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 (E)-3,7-dimethyl-2-octene-1,8-diol
  参考文献：
  名称：

  Asymmetric synthesis of (E)- and (Z)-3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid

  摘要：

  Both enantiomers and regioisomers of (E)- and (Z)-3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid, which have important biological activity were synthesized by enzymatic transesterification of primary alcohols (E)- and (Z)-10. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.032

文献信息

• BAKER’S YEAST HYDROGENATION OF CARBONYL ACTIVATED DOUBLE BONDS. ENANTIOSELECTIVE SYNTHESIS OF THE (<i>S</i>)-FORM OF THE DIHYDROTERPENEDIOL SECRETED BY<i>DANAUS CHRYSIPPUS</i>AND OF A PHEROMONE OF<i>CALLOSOBRUCHUS CHINENSIS</i>L.
  作者：Paola Gramatica、Giuseppe Giardina、Giovanna Speranza、Paolo Manitto

  DOI：10.1246/cl.1985.1395

  日期：1985.9.5

  The (S)-forms of (E)-3,7-dimethyl-2-octene-1,8-diol (secreted by male danaid butterflies) and of (E)-3,7-dimethyl-2-octene-1,8-dioic acid (a pheromone of the azuki bean weevil) were synthesized via stereoselective hydrogenation by baker’s yeast of the carbonyl activated double bond of achiral precursors.

  通过面包酵母对非手性前体的羰基活化双键进行立体选择性氢化，合成了(E)-3,7-二甲基-2-辛烯-1,8-二醇（雄性丹顶鹤蝶分泌）和(E)-3,7-二甲基-2-辛烯-1,8-二酸（红豆象鼻虫的一种信息素）的(S)-形式。
• Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male danaus chrysippus (African monarch)
  作者：Kunihiko Takabe、Nobuyuki Mase、Hiroya Hashimoto、Atsushi Tsuchiya、Takashi Ohbayashi、Hidemi Yoda

  DOI：10.1016/s0960-894x(03)00352-4

  日期：2003.6

  The synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (1), which was isolated from the hairpencils of male Danaus chrysippus (African Monarch), was investigated. The key step of the sequence involves asymmetric desymmetrization of the 1,3-propanediol 7 with lipase, in which high enantio selectivity was observed. Total synthesis afforded (S)-1 in 12 steps and 26% overall yield from readily available geraniol. (C) 2003 Elsevier Science Ltd. All rights reserved.
• GIERSCH, WOLFGANG;SCHULTE-ELTE, KARL H., HELV. CHIM. ACTA, 73,(1990) N, C. 733-738
  作者：GIERSCH, WOLFGANG、SCHULTE-ELTE, KARL H.

  DOI：——

  日期：——
• Asymmetric synthesis of (E)- and (Z)-3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid
  作者：S. Nanda、A.Ian Scott

  DOI：10.1016/j.tetasy.2004.01.032

  日期：2004.3

  Both enantiomers and regioisomers of (E)- and (Z)-3,7-dimethyl-2-octene-1,8-diol and callosobruchusic acid, which have important biological activity were synthesized by enzymatic transesterification of primary alcohols (E)- and (Z)-10. (C) 2004 Elsevier Ltd. All rights reserved.