(+/-)-cadinene dihydrochloride | 481-35-6

• 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: (+/-)-cadinene dihydrochloride
• 英文别名: rac-4,10-dichloro-4βH,10βH-cadinane；rac-4,10-Dichlor-4βH,10βH-cadinan；(+/-)-Cadinen Dihydrochlorid；(+/-)-Cadinen-dihydrochlorid；(+/-)-Cadien-dihydrochlorid；(9AlphaH,10beta,IH)-1beta,6beta-dichloro-1alpha,6alpha-dimethyl-4beta-isopropylperhydronaphthalene；(1R,4R,4aS,7R,8aR)-4,7-dichloro-4,7-dimethyl-1-propan-2-yl-1,2,3,4a,5,6,8,8a-octahydronaphthalene
• CAS: 481-35-6
• 化学式: C₁₅H₂₆Cl₂
• 分子量: 277.277
• InChiKey: MVELFXADPKFEEW-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,2,3,4,5,8-Hexahydro-1-hydroxy-4-isopropyl-6-methoxy-naphthalin 在 aluminum isopropoxide 作用下， 生成 (+/-)-cadinene dihydrochloride
  参考文献：
  名称：

  倍半萜烯的研究—XXIV：（±）-二氢化卡宾烯盐酸盐的合成

  摘要：

  据报道，全合成的（±）-4-异丙基-反式-癸烷-1,6-二酮是卡丁烷系列中的关键中间体，并已转化为（±）-卡丹烯二盐酸盐。

  DOI：

  10.1016/s0040-4020(01)82270-5

文献信息

• Stereospecific total synthesis of (+)-ε- and (-)-γ2-cadinene
  作者：Lâle Aka Burk、Milton D. Soffer

  DOI：10.1016/0040-4020(76)85113-7

  日期：——

  (+)-ε-Cadinene (1) and (-)-γ2cadinene (2) have been synthesized from the enol ether ketone 3 via the methylene ketone 4. These two stereospecific total syntheses confirm the structures assigned to these sesquiterpenes and represent the first preparation by totally synthetic methods of any of the widespread group of cadinanes in their native state.

  （+） - ε杜松烯（1）和（ - ） - γ 2杜松烯（2）已经从烯醇醚酮合成3经由亚甲基酮4。这两种立体有特异性的总合成证实了分配给这些倍半萜的结构，并且代表了通过完全合成方法制备的处于其原始状态的任何广泛的卡地那汀的第一种制备方法。
• Terpenoids—XXXVIII
  作者：C.C. Kartha、P.S. Kalsi、A.M. Shaligram、K.K. Chakravarti、S.C. Bhattacharyya

  DOI：10.1016/0040-4020(63)80027-7

  日期：1963.1

  A new sesquiterpene hydrocarbon, (−)γ2-cadinene, has been isolated from Indian vetiver oil. On the basis of formation of (+) cadinene dihydrochloride and other reactions, its structure and absolute configuration are represented by the formula I. It belongs to the unusual antipodal group of cadinenes.

  一种新的倍半萜烃类，（ - ）γ 2 -cadinene，已经从印度香根草油分离。在形成（+）盐酸二氢卡丁烯的反应和其他反应的基础上，其结构和绝对构型由式I表示。它属于异常的cadinenes对映体基团。
• Terpenoids—XXXVI
  作者：A.A. Rao、K.L. Surve、K.K. Chakravarti、S.C. Bhattacharyya

  DOI：10.1016/0040-4020(63)80026-5

  日期：1963.1

  Khusinol, a new crystalline secondary sesquiterpene alcohol, isolated from North Indian vetiver oil (Vetiveria zizaniodes, Linn) is shown to have the absolute configuration represented by the structure XX on the basis of degradative experiments and its conversion to (−)-γ-cadinene under mild conditions. It belongs to the unusual antipodal group of cadinenes. γ1-Cadinene(XXI) isolated from Malabar lemongrass

  从北部印度香根草油（Vetiveria zizaniodes，Linn）中分离出的一种新的结晶型倍半萜烯醇Khusinol在降解实验及其转化为（-）-γ-cadinene的基础上，具有由结构XX表示的绝对构型在温和的条件下。它属于cadinenes的反对立群。γ 1 -Cadinene（XXI）从马拉巴香茅油分离也已经显示到属于同一对映组。
• A Synthetic Approach To Cadinane- and Amorphane-Type Sesquiterpenoids via Annelation Of Cyclohexanone Derivatives With (<i>E</i>)-2-Methyl-3-hepten-5-one. A Simple Synthesis of (±)-Cadinene Dihydrochloride
  作者：Edward Piers、Wynona M. Phillips-Johnson

  DOI：10.1139/v75-176

  日期：1975.5.1

  The annelation of the pyrrolidine enamine of cyclohexanone with (E)-2-methyl-3-hepten-5-one (7) afforded a 7:3 mixture of the octalones 12 and 13. Lithium–ammonia reduction of the former afforded the trans-fused decalone 14, whereas, in contrast, a similar reduction of 13 gave exclusively the cis-fused decalone 16. Annelation of the pyrrolidine enamine of 4-hydroxy-cyclohexanone with the unsaturated ketone 7 yielded a 7:3 mixture of the octalones 22 and 23. The former was converted via a short, efficient synthetic sequence into (±)-cadinene dihydrochloride (30).

  环己酮的吡咯烷烯胺与(E)-2-甲基-3-庚烯-5-酮(7)的消除反应生成了八环酮12和13的7:3混合物。前者经锂-氨还原反应生成反式螺环十酮14，而后者则通过相似的还原反应仅生成顺式螺环十酮16。4-羟基环己酮的吡咯烷烯胺与不饱和酮7的环化反应产生了八环酮22和23的7:3混合物。前者通过简短高效的合成途径转化为(±)-卡丁烯二盐酸盐(30)。
• Terpenoids—xl
  作者：P.S. Kalsi、K.K. Chakravarti、S.C. Bhattacharyya

  DOI：10.1016/s0040-4020(01)99362-7

  日期：1963.1

  Khusol, a crystalline primary sesquiterpene alcohol, C15H24O, isolated from North Indian vetiver oil has been assigned the structure and absolute configuration represented by I. It belongs to the antipodal group of cadinenic alcohols.

  从印度北部香根草油中分离得到的Khusol（一种结晶的倍半萜烯醇，C 15 H 24 O）已被赋予I所示的结构和绝对构型。