(-)-3α-chloro-4βH-eudesm-11,12-ene | 200343-76-6

• 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: (-)-3α-chloro-4βH-eudesm-11,12-ene
• 英文别名: (3R,4S,4aS,6R,8aS)-3-chloro-4,8a-dimethyl-6-prop-1-en-2-yl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalene
• CAS: 200343-76-6
• 化学式: C₁₅H₂₅Cl
• 分子量: 240.816
• InChiKey: UZIPBEZNIFJCHE-ZQNQSHIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (-)-3α-chloro-4βH-eudesm-11,12-ene 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以86%的产率得到α-芹子烯
  参考文献：
  名称：

  Total synthesis and stereochemistry of 13-hydroxy-α-eudesmol

  摘要：

  The first total synthesis of both C-11 epimers of 13-hydroxy-alpha-eudesmol 1a and 1b by the use, as a key reaction, of the Sharpless asymmetric dihydroxylation of alkene 7 is presented. The absolute configuration of natural 13-hydroxy-alpha-eudesmol is established through comparison of the H-1 NMR spectrum of natural diol and synthetic diols. In our synthesis another natural product (+)-alpha-selinene 2 has also been accomplished. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00184-0
• 作为产物：
  描述：

  (-)-dihydro-α-cyperol 在 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以88%的产率得到(-)-3α-chloro-4βH-eudesm-11,12-ene
  参考文献：
  名称：

  (+)-菊酚的首次全合成

  摘要：

  已经描述了从 (+)-二氢香芹酮 (4) 开始的 (+)-菊酚 (1) 的首次全合成。我们合成的特点是高产率地将 C-3-C-4 双键引入eudesmane 骨架和由 BF3 促进环氧化物重排为烯丙醇。OEt2-Bu4NI 试剂。在我们的合成中，(+)-α-eudesmol (5) 已被用作关键中间体。

  DOI：

  10.1246/cl.1997.1289

文献信息

• First Total Synthesis of (+)-Chrysanthemol
  作者：Yonggang Chen、Zhaoming Xiong、Gang Zhou、Jiong Yang、Yulin Li

  DOI：10.1246/cl.1997.1289

  日期：1997.12

  The first total synthesis of (+)-chrysanthemol (1) has been described starting from (+)-dihydrocarvone (4). The features of our synthesis are the high yield introduction of C-3-C-4 double bond into eudesmane skeleton and rearrangement of epoxide to allylic alcohol promoted by BF3 . OEt2-Bu4NI reagent. In our synthesis, (+)-alpha-eudesmol (5) has been used as a key intermediate.

  已经描述了从 (+)-二氢香芹酮 (4) 开始的 (+)-菊酚 (1) 的首次全合成。我们合成的特点是高产率地将 C-3-C-4 双键引入eudesmane 骨架和由 BF3 促进环氧化物重排为烯丙醇。OEt2-Bu4NI 试剂。在我们的合成中，(+)-α-eudesmol (5) 已被用作关键中间体。
• Total synthesis and stereochemistry of 13-hydroxy-α-eudesmol
  作者：Yonggang Chen、Zhaoming Xiong、Gang Zhou、Lijun Liu、Yulin Li

  DOI：10.1016/s0957-4166(98)00184-0

  日期：1998.6

  The first total synthesis of both C-11 epimers of 13-hydroxy-alpha-eudesmol 1a and 1b by the use, as a key reaction, of the Sharpless asymmetric dihydroxylation of alkene 7 is presented. The absolute configuration of natural 13-hydroxy-alpha-eudesmol is established through comparison of the H-1 NMR spectrum of natural diol and synthetic diols. In our synthesis another natural product (+)-alpha-selinene 2 has also been accomplished. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An Efficient Synthetic Strategy for Introduction of C₃-C₄Double Bond into Eudesmane Skeleton: First Total Synthesis of (+)-Chrysanthemol
  作者：Yonggang Chen、Gang Zhou、Zhaoming Xiong、Lijun Liu、Yulin Li

  DOI：10.1002/jccs.200100042

  日期：2001.4

  The first enantioselective synthesis of (+)-chrysanthemol 1 was carried out starting from (+)-dihydrocarvone in ten steps. In our studies, a facile synthetic strategy has been developed for introduction of C3-C4 double bond into a eudesmane skeleton.

  (+)-菊酚 1 的第一次对映选择性合成是从 (+)-二氢香芹酮开始分十步进行的。在我们的研究中，已经开发了一种简便的合成策略，用于将 C3-C4 双键引入 eudesmane 骨架。