5-(2,2-dimethylcyclopropyl)-3-methylpentan-1-ol | 321858-86-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(2,2-dimethylcyclopropyl)-3-methylpentan-1-ol
• CAS: 321858-86-0
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: ZLTVXXPIVAXMEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  香茅醇 、 二溴甲烷 在 三异丁基铝 、 iron(III) chloride 作用下， 反应 3.25h， 以98%的产率得到5-(2,2-dimethylcyclopropyl)-3-methylpentan-1-ol
  参考文献：
  名称：

  三异丁基铝在二溴甲烷中非活化烯烃的过渡金属催化环丙烷化反应

  摘要：

  非活化烯烃与廉价三异丁基铝 (TIBA) 的环丙烷化反应，在二溴甲烷作为溶剂和试剂中，在环境温度下由 FeCl3 有效催化。CuI盐、CpTiCl3和[CpFe(CO)2]2的催化量同样有效。可捕集过量TIBA骤冷后产生的2-甲基丙烷，回收过量二溴甲烷，具有工业应用价值。不饱和羰基化合物的无溶剂 DIBAH 或 TIBA 还原，然后不饱和铝醇化物在二溴甲烷中的原位 TIBA 环丙烷化得到环丙基链烷醇。二烯醇，例如香叶醇、芳樟醇或正菘醇在其远端位置被选择性地环丙烷化，这允许合成风味和香味化合物，例如 Δ-柠檬醛、顺式-javanol 和 7-甲基-乔木。

  DOI：

  10.1002/ejoc.201100528

文献信息

• NOVEL JUVENILE HORMONE ANALOGUES AND THEIR USE AS ANTIFOULING AGENTS
  申请人：Bioparken AS

  公开号：EP1204320A2

  公开（公告）日：2002-05-15
• CITRAL AND CITRONELLAL DERIVATIVES
  申请人：Turin Luca

  公开号：US20090016976A1

  公开（公告）日：2009-01-15

  Improved citral and citronellal derivatives, and fragrance and flavorings including the derivatives, that have a longer useful shelf life than citral and citronellal and/or fragrances and flavoring including citral and citronellal, are disclosed. In particular, the derivatives maintain the fragrance characteristics of citral and citronellal, while lowering the allergic properties, and lemony flavors and fragrances with a longer shelf-life than citral and citronellal, are disclosed. Also discovered are methods of making the derivatives, and articles of manufacture including the derivatives. The derivatives replace the aldehyde group in citral or citronellal with a hydroxy group. In one embodiment, the derivatives also replaced one or more double bonds in citral or the double bond in citronellal with a cyclopropyl group, which can be unsubstituted, or substituted with one or two alkyl, preferably methyl, groups, or with an oxirane or thiirane ring or combinations thereof. The alkyl groups in the cyclopropyl groups can optionally be substituted, for example, with electron donating groups, electron withdrawing groups, groups which increase the hydrophilicity or hydrophobicity, and the like. Examples of suitable articles of manufacture include candles, air fresheners, perfumes, disinfectant compositions, hypochlorite (bleach) compositions, beverages such as beer and soda, denture cleanser tablets and flavored orally-delivered products such as lozenges, candies, and the like.
• [EN] NOVEL JUVENILE HORMONE ANALOGUES AND THEIR USE AS ANTIFOULING AGENTS<br/>[FR] NOUVEAUX ANALOGUES DE L'HORMONE JUVENILE UTILISES COMME AGENTS ANTI-SALISSURES
  申请人：FORSKNINGSPARKEN I AAS AS

  公开号：WO2001006853A2

  公开（公告）日：2001-02-01

  The use of juvenile hormone analogues (juvenoids, juvenile hormone-like compounds, juvenile hormone mimics) compounds as antifouling agents in e.g. paint compositions for ships and immersed structures including oil drilling rigs and fish nets and novel juvenile hormone compounds. The compounds are active against barnacles including species of Cirripedia such as Balanus species and prevent crucial steps in the process of barnacle fouling on solid surfaces such as the settlement, attachment and/or metamorphosis of barnacle cyprid larvae.