Epi-Carrisone | 547-27-3

• 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: Epi-Carrisone
• 英文别名: (4aR,7R)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 547-27-3
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: ZWSWPQHKDLDIDL-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Epi-Carrisone 在 dichloroalane 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 表桉叶油醇
  参考文献：
  名称：

  An efficient stereocontrolled synthesis of (−)-10-epi-5β,11-dihydroxyeudesmane and (−)-4,10-epi-5β,11-dihydroxyeudesmane

  摘要：

  A concise and efficient synthesis of (-)-10-epi-5 beta, 11-dihydroxyeudesmane 1 and (-)-4,10-epi-5 beta, 11-dihydroxyeudesmane 2, via (-)-10-epi-gamma-eudesmol 5, was accomplished starting from (+)-dihydrocarvone. The salient feature of our synthesis is the utilization of substrate-directable epoxidation and homogeneous hydrogenation to control the stereochemistry at the C-4 and C-5 positions of the title compounds. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00141-4
• 作为产物：
  描述：

  (+)-二氢香芹酮 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 Epi-Carrisone
  参考文献：
  名称：

  (+)-Occidentalol: Absolute Stereostructure and Total Synthesis

  摘要：

  从(+)-二氢香茅酮(3)和(+)-西洋香叶醇(2)中制备了羟基酮7，从而确定了后者的绝对立体结构。将化合物7转化为(+)-西洋香叶醇的三阶段反应构成了倍半萜的全合成。

  DOI：

  10.1139/v72-051

文献信息

• Stereoselectivity in microbiological transformation of stereoisomers of .ALPHA.- cyperone and dihydro-.ALPHA.-cyperone with Colletotrichum phomoides.
  作者：HIROSHI HIKINO、CHOHACHI KONNO、YAYOI IKEDA、NOBUKO IZUMI、TSUNEMATSU TAKEMOTO

  DOI：10.1248/cpb.23.1231

  日期：——

  Incubation of three stereoisomers of α-cyperone (1, 2, and 3) with Colletotrichum phomoides resulted in two types of modification hydroxylation (C-2 and C-6) in one isomer (2) and dehydrogenation (C-6 : C-7) in another isomer (3) at the nuclei and in three types of modification (hydration to an alcohol, allylic hydroxylation to an allyl alcohol, and oxidation to a 1, 2-glycol) at the side chains in all the isomers in different rates. On fermentation with the same microbe of three stereoisomers of dihydro-α-cyperone (16, 17, and 18), prepared for prevention of the side chain modification, hydroxylation at the nucleus (C-1) occurred merely in one isomer (16), and the same types of oxidation at the side chains also took place in all the isomers as in their congeners (1-3). The stereoselectivity and the probable mechanisms of the transformations are discussed.

  将三种立体异构体α-赛普酮（1、2和3）与Colletotrichum phomoides共培养后，在其中一种异构体（2）中发生了两种类型的修改羟基化（C-2和C-6），而在另一种异构体（3）中发生了去氢反应（C-6 : C-7），在所有异构体的侧链中以不同速率发生了三种类型的修改（转化为醇、烯丙羟基化为烯丙醇，以及氧化为1, 2-甘醇）。在与同一微生物共同发酵三种双氢α-赛普酮的立体异构体（16、17和18）时，为了防止侧链修改，羟基化仅在一种异构体（16）的核部位（C-1）发生，而在所有异构体的侧链中也发生了与其同源物（1-3）相同类型的氧化反应。讨论了转化的立体选择性和可能的机制。
• Total Synthesis of (+)-Occidentalol
  作者：M. Sergent、M. Mongrain、P. Deslongchamps

  DOI：10.1139/v72-050

  日期：1972.2.1

  A synthesis of (+)-occidentalol (1) has been realized in six steps, starting from the readily available enonealcohol 3.

  从易得的烯醇3出发，经过六步反应，成功合成了(+)-occidentalol (1)。
• An efficient stereocontrolled synthesis of (−)-10-epi-5β,11-dihydroxyeudesmane and (−)-4,10-epi-5β,11-dihydroxyeudesmane
  作者：Zhaoming Xiong、Gang Zhou、Jiong Yang、Yonggang Chen、Yulin Li

  DOI：10.1016/s0957-4166(98)00141-4

  日期：1998.5

  A concise and efficient synthesis of (-)-10-epi-5 beta, 11-dihydroxyeudesmane 1 and (-)-4,10-epi-5 beta, 11-dihydroxyeudesmane 2, via (-)-10-epi-gamma-eudesmol 5, was accomplished starting from (+)-dihydrocarvone. The salient feature of our synthesis is the utilization of substrate-directable epoxidation and homogeneous hydrogenation to control the stereochemistry at the C-4 and C-5 positions of the title compounds. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• (+)-Occidentalol: Absolute Stereostructure and Total Synthesis
  作者：Young Amano、Clayton H. Heathcock

  DOI：10.1139/v72-051

  日期：1972.2.1

  Hydroxy ketone 7 has been prepared from both (+)-dihydrocarvone (3) and (+)-occidentalol (2), thus establishing the absolute stereostructure of the latter. The three-stage conversion of compound 7 into (+)-occidentalol constitutes a total synthesis of the sesquiterpene.

  从(+)-二氢香茅酮(3)和(+)-西洋香叶醇(2)中制备了羟基酮7，从而确定了后者的绝对立体结构。将化合物7转化为(+)-西洋香叶醇的三阶段反应构成了倍半萜的全合成。