(1E,5E,9E)-1,5,9-trimethyl-12-(propan-2-ylidene)cyclotetradeca-1,5,9-triene | 62824-13-9

• 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: (1E,5E,9E)-1,5,9-trimethyl-12-(propan-2-ylidene)cyclotetradeca-1,5,9-triene
• 英文别名: cembrene C；(1E,5E,9E)-1,5,9-trimethyl-12-propan-2-ylidenecyclotetradeca-1,5,9-triene
• CAS: 62824-13-9
• 化学式: C₂₀H₃₂
• 分子量: 272.474
• InChiKey: SHVZFTWRFOQOFU-GDVLXBNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (-)-西松烧酹醇 在 吡啶 、 三氯氧磷 作用下， 生成 (1E,5E,9E)-1,5,9-trimethyl-12-(propan-2-ylidene)cyclotetradeca-1,5,9-triene
  参考文献：
  名称：

  Herin,M.; Tursch,B., Bulletin des Societes Chimiques Belges, 1976, vol. 85, p. 707 - 719

  摘要：

  DOI：

文献信息

• Marine terpenes and terpenoids. VII. Minor cembranoid derivatives, structurally related to the potent anti-tumor-promoter sarcophytol A, from the soft coral Sarcophyton glaucum.
  作者：Masaru KOBAYASHI、Katsunori OSABE

  DOI：10.1248/cpb.37.631

  日期：——

  Eight new cembranoids, sarcophytol M (3), sarcophytol N (9a), sarcophytol J (11a), sarcophytol H and its diacetate (15a and 15b), sarcophytol O (18), sarcophytol I (19a) and sarcophytol G (24a), and known cembranoids nephthenol (7) and sinulariol D (8), were isolated from the soft coral Sarcophyton glaucum.Their structures were determined from the spectroscopic properties and by chemical conversion.Sarcophytol M (3) was found to be the enantiomer of the known compound cembrenol from a terrestrial plant.Sarcophytol N (9a) and sarcophytol J (11a) were the geometrical isomers at C-3 of the major components sarcophytol A (1a) and sarcophytol B (2a), which are potent anti-tumor-promoters.Sarcophytol H and sarcophytol O were identical with the diols 15a and 18, respectively, which were previously synthesized from 1a.Sarcophytol I (19a) and sarcophytol G (24a) were the diastereoisomers of the known compounds sarcophytol E (22a) and sarcophytol D (21a), respectively, and their absolute configurations were determined by chemical conversion of two 11, 12E-epoxides (20 and 23).

  八种新西松烷类化合物：肌醇 M (3)、肌醇 N (9a)、肌醇 J (11a)、肌醇 H 及其二乙酸酯（15a 和 15b）、肌醇 O (18)、肌醇 I (19a) 和肌醇 G (24a) 、以及已知的西松烷类化合物 nephthenol (7) 和 Sinulariol D (8)，是从软珊瑚 Sarcophyton glaucum 中分离出来的。它们的结构是通过光谱特性和化学转化确定的。Sarcophytol M (3) 被发现是其对映体来自陆地植物的已知化合物西柏烯醇。 Sarcophytol N (9a) 和 sarcophytol J (11a) 是主要成分 sarcophytol A (1a) 和 sarcophytol B (2a) 的 C-3 几何异构体，它们具有有效的抗肿瘤作用Sarcophytol H 和 sarcophytol O 分别与之前从 1a 合成的二醇 15a 和 18 相同。 Sarcophytol I (19a) 和 sarcophytol G (24a) 是已知化合物 sarcophytol E (22a) 和 sarcophytol 的非对映异构体D (21a) 分别，其绝对构型通过两种 11、12E-环氧化物（20 和 23）的化学转化确定。
• Identification and Characterization of Bacterial Diterpene Cyclases that Synthesize the Cembrane Skeleton
  作者：Ayuko Meguro、Takeo Tomita、Makoto Nishiyama、Tomohisa Kuzuyama

  DOI：10.1002/cbic.201200651

  日期：2013.2.11

  Digging up skeletons: We report the identification and the functional characterization of two terpene cyclases (DtcycA and DtcycB) that were mined from the genome of Streptomyces sp. SANK 60404. DtcycA and DtcycB are novel bacterial diterpene cyclases for the synthesis of the cembrane skeleton.

  挖掘骨骼：我们报告了从Streptomyces sp.基因组中挖掘的两种萜烯环化酶（DtcycA 和 DtcycB）的鉴定和功能表征。SANK 60404. DtcycA 和 DtcycB 是用于合成膜骨架的新型细菌二萜环化酶。
• KOBAYASHI, MASARU;OSABE, KATSUNORI, CHEM. AND PHARM. BULL., 37,(1989) N, C. 631-636
  作者：KOBAYASHI, MASARU、OSABE, KATSUNORI

  DOI：——

  日期：——