7-Methoxycadalene | 87843-24-1

• 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: 7-Methoxycadalene
• 英文别名: 6-Methoxy-4,7-dimethyl-1-(propan-2-yl)naphthalene；7-methoxy-1,6-dimethyl-4-propan-2-ylnaphthalene
• CAS: 87843-24-1
• 化学式: C₁₆H₂₀O
• 分子量: 228.334
• InChiKey: CTYYPXUXVBFGNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-Methoxycadalene 在 4-二甲氨基吡啶 、 sodium hydride 、 乙硫醇 作用下， 以 二氯甲烷 、 paraffin oil 为溶剂， 反应 5.0h， 生成 (R)-5-isopropyl-3,8-dimethyl-5,6-dihydronaphthalen-2-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Stereochemical investigation and total synthesis of inuloidin, a biologically active sesquiterpenoid from Heterotheca inuloides

  摘要：

  The stereochemistry of inuloidin (1), which was a sesquiterpenoid that was characterized as a plant growth inhibitory substance from Heterotheca inuloides, was investigated. The modified Mosher's method coupled with a total synthetic study using osmium oxidation and Burgess dehydration as key steps were performed to clarify the stereochemistry of 1, which was determined to be a 2S,4R isomer. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.057
• 作为产物：
  描述：

  (Z)-6-(3-methoxy-4-methylphenyl)-2-methylhept-2-en-1-ol 在 N-氯代丁二酰亚胺 、 二甲基硫 、 zinc(II) chloride 作用下， 生成 7-Methoxycadalene
  参考文献：
  名称：

  通过13-羟基黄嘌呤唑（一种帕维夫林的可能的前体）合成羟基cadalene和hydroxycalamenene

  摘要：

  从苯乙酮衍生物开始，合成了三个倍半萜烯，黄嘌呤酚，羟基cadalene和羟基cal烯。parvifolin的仿生形成无法实现。

  DOI：

  10.1016/s0040-4039(00)96151-3

文献信息

• Lindahl, Annales Academiae Scientiarum Fennicae, Series A2: Chemica, 1953, # 48, p. 51
  作者：Lindahl

  DOI：——

  日期：——
• KRAUSE, W.;BOHLMANN, F., TETRAHEDRON LETT., 28,(1987) N 23, 2575-2578
  作者：KRAUSE, W.、BOHLMANN, F.

  DOI：——

  日期：——
• Gossypium cadinanes and their analogs: synthesis of lacinilene C, 2,7-dihydroxycadalene, and their methyl ethers
  作者：John P. McCormick、Teruo Shinmyozu、J. Paul Pachlatko、Tann R. Schafer、Jeffrey W. Gardner、Robert D. Stipanovic

  DOI：10.1021/jo00175a007

  日期：1984.1
• Stereochemical investigation and total synthesis of inuloidin, a biologically active sesquiterpenoid from Heterotheca inuloides
  作者：Jumpei Kamatani、Takehiro Iwadate、Reiko Tajima、Hideaki Kimoto、Yoichi Yamada、Noriyoshi Masuoka、Isao Kubo、Ken-ichi Nihei

  DOI：10.1016/j.tet.2014.03.057

  日期：2014.5

  The stereochemistry of inuloidin (1), which was a sesquiterpenoid that was characterized as a plant growth inhibitory substance from Heterotheca inuloides, was investigated. The modified Mosher's method coupled with a total synthetic study using osmium oxidation and Burgess dehydration as key steps were performed to clarify the stereochemistry of 1, which was determined to be a 2S,4R isomer. (c) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of hydroxycadalene and hydroxycalamenene via 13-hydroxyxanthorrhizol, a possible precursor of parvifolin
  作者：Wolfgang Krause、Ferdinand Bohlmann

  DOI：10.1016/s0040-4039(00)96151-3

  日期：1987.1

  Starting with an acetophenone derivative three sesquiterpenes, xanthorrhizol, hydroxycadalene and hydroxycalamenene were synthesized. The biomimetic formation of parvifolin could not be achieved.

  从苯乙酮衍生物开始，合成了三个倍半萜烯，黄嘌呤酚，羟基cadalene和羟基cal烯。parvifolin的仿生形成无法实现。