(Z)-(1S,5R,11S)-8-Hydroxymethyl-1-methyl-5-(4-methyl-pent-3-enyl)-4-oxo-12-oxa-bicyclo[9.1.0]dodec-7-ene-5-carboxylic acid methyl ester | 609767-81-9

• 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: (Z)-(1S,5R,11S)-8-Hydroxymethyl-1-methyl-5-(4-methyl-pent-3-enyl)-4-oxo-12-oxa-bicyclo[9.1.0]dodec-7-ene-5-carboxylic acid methyl ester
• 英文别名: methyl (1S,5R,7Z,11S)-8-(hydroxymethyl)-1-methyl-5-(4-methylpent-3-enyl)-4-oxo-12-oxabicyclo[9.1.0]dodec-7-ene-5-carboxylate
• CAS: 609767-81-9
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: SYCASLNTEUNNRV-JOWVMDMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(1S,5R,11S)-8-Hydroxymethyl-1-methyl-5-(4-methyl-pent-3-enyl)-4-oxo-12-oxa-bicyclo[9.1.0]dodec-7-ene-5-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (4Z,8E)-(1S,7S,11S)-7,11-Dimethyl-7-(4-methyl-pent-3-enyl)-12-oxa-bicyclo[9.1.0]dodeca-4,8-diene-4-carbaldehyde
  参考文献：
  名称：

  Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex

  摘要：

  The absolute configuration of vibsanin F (1), one of the simplest 11-membered ring vibsane-type diterpene, was established to be 6R, 7S and 11S by asymmetric synthesis. A diastereomer (1a) with a 6S, 7S and 11S configuration was synthesized starting from myrcene by procedures featuring a Sharpless asymmetric epoxidation and a high diastereoselective eleven-membered ring formation between a pi-allylpalladium complex and a beta-ketoester nucleophile. Subsequent reduction of epoxide in la with LiAlH4 gave a diol, which was identical with that derived from vibsanin F. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01537-5
• 作为产物：
  描述：

  8-羟基-7-甲基-3-亚甲基-1,6-(E)-辛二烯 在 titanium(IV) isopropylate 、 四(三苯基膦)钯 叔丁基过氧化氢 、 15-冠醚-5 、 L-(+)-酒石酸二乙酯 、 三氟甲磺酸酐 、 4 A molecular sieve 、 sodium hydride 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (Z)-(1S,5R,11S)-8-Hydroxymethyl-1-methyl-5-(4-methyl-pent-3-enyl)-4-oxo-12-oxa-bicyclo[9.1.0]dodec-7-ene-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex

  摘要：

  The absolute configuration of vibsanin F (1), one of the simplest 11-membered ring vibsane-type diterpene, was established to be 6R, 7S and 11S by asymmetric synthesis. A diastereomer (1a) with a 6S, 7S and 11S configuration was synthesized starting from myrcene by procedures featuring a Sharpless asymmetric epoxidation and a high diastereoselective eleven-membered ring formation between a pi-allylpalladium complex and a beta-ketoester nucleophile. Subsequent reduction of epoxide in la with LiAlH4 gave a diol, which was identical with that derived from vibsanin F. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01537-5

文献信息

• Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex
  作者：Hiroaki Yuasa、Gouki Makado、Yoshiyasu Fukuyama

  DOI：10.1016/s0040-4039(03)01537-5

  日期：2003.8

  The absolute configuration of vibsanin F (1), one of the simplest 11-membered ring vibsane-type diterpene, was established to be 6R, 7S and 11S by asymmetric synthesis. A diastereomer (1a) with a 6S, 7S and 11S configuration was synthesized starting from myrcene by procedures featuring a Sharpless asymmetric epoxidation and a high diastereoselective eleven-membered ring formation between a pi-allylpalladium complex and a beta-ketoester nucleophile. Subsequent reduction of epoxide in la with LiAlH4 gave a diol, which was identical with that derived from vibsanin F. (C) 2003 Elsevier Ltd. All rights reserved.