(1S,2E,4Z,7E,10R,11E)-Cembra-2,4,7,11-tetraen-10-ol | 81522-05-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2E,4Z,7E,10R,11E)-Cembra-2,4,7,11-tetraen-10-ol
• 英文别名: 10-hydroxycembrene；(10R)-10-Hydroxycembrene；(1R,2E,6S,7E,9Z,12E)-3,9,13-trimethyl-6-propan-2-ylcyclotetradeca-2,7,9,12-tetraen-1-ol
• CAS: 81522-05-6
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: UISPGBUXWMMCCP-HPGSRRKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2E,4Z,7E,10R,11E)-Cembra-2,4,7,11-tetraen-10-ol 在 lithium 、 乙胺 作用下， 以 吡啶 为溶剂， 生成 4,8,12-Trimethyl-1-isopropyl-Δ^2,7,11-cyclotetradecatrien; Dihydrocembren 2
  参考文献：
  名称：

  10-OXO-, 10-HYDROXY-, AND 10-METHOXYCEMBRENES FROM THE SOFT CORALSARCOPHYTA ELEGANS

  摘要：

  报告了从软珊瑚 Sarcophyta elegans 中分离出的 10-氧代、10-羟代和 10-甲氧基塞姆布兰内酯的结构和绝对构型。

  DOI：

  10.1246/cl.1983.1719
• 作为产物：
  描述：

  (2E,5E,8Z,10E)-(1S,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-2,5,8,10-tetraenol 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 (1S,2E,4Z,7E,10R,11E)-Cembra-2,4,7,11-tetraen-10-ol
  参考文献：
  名称：

  Conformational analysis of the 10- and 13-hydroxy derivatives of cembrene

  摘要：

  Conformational analysis of 10- and 13-hydroxycembrenes 4, 5, 7, and 8 has been carried out using NMR methods and molecular mechanics calculations. The results indicate that the conformational states of all investigated compounds in solution are characterized by the same orientation of double bonds with respect to the average plane of the macrocycle. Alcohols 4 and 8 are conformationally homogeneous, and their solution conformations correspond to the known solution (and crystal) conformation of cembrene (1). In the case of alcohols 5 and 7, there is additional conformational flexibility in the C(8)-C(11) molecular fragment. The influence of simple substituent (hydroxy group) effects and an intramolecular OH* pi-hydrogen bond on conformational states of the cembranoids are discussed.

  DOI：

  10.1021/jo00106a015

文献信息

• Conformational analysis of the 10- and 13-hydroxy derivatives of cembrene
  作者：Alexey V. Vorobjev、Makhmut M. Shakirov、Victor A. Raldugin、Clayton H. Heathcock

  DOI：10.1021/jo00106a015

  日期：1995.1

  Conformational analysis of 10- and 13-hydroxycembrenes 4, 5, 7, and 8 has been carried out using NMR methods and molecular mechanics calculations. The results indicate that the conformational states of all investigated compounds in solution are characterized by the same orientation of double bonds with respect to the average plane of the macrocycle. Alcohols 4 and 8 are conformationally homogeneous, and their solution conformations correspond to the known solution (and crystal) conformation of cembrene (1). In the case of alcohols 5 and 7, there is additional conformational flexibility in the C(8)-C(11) molecular fragment. The influence of simple substituent (hydroxy group) effects and an intramolecular OH* pi-hydrogen bond on conformational states of the cembranoids are discussed.
• 10-OXO-, 10-HYDROXY-, AND 10-METHOXYCEMBRENES FROM THE SOFT CORAL<i>SARCOPHYTA ELEGANS</i>
  作者：Yasuto Uchio、Masayoshi Nitta、Hiroshi Nozaki、Mitsuru Nakayama、Tetsuo Iwagawa、Tsunao Hase

  DOI：10.1246/cl.1983.1719

  日期：1983.11.5

  The structures and absolute configurations of three cembranoids, 10-oxo-, 10-hydroxy-, and 10-methoxycembrenes, isolated from the soft coral Sarcophyta elegans, are reported.

  报告了从软珊瑚 Sarcophyta elegans 中分离出的 10-氧代、10-羟代和 10-甲氧基塞姆布兰内酯的结构和绝对构型。