4-isopropylidene-cyclohexanol | 175020-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-isopropylidene-cyclohexanol
• 英文别名: 4-propan-2-ylidenecyclohexan-1-ol
• CAS: 175020-74-3
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: BHGNYQMQMOKBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 4-isopropylidene-cyclohexanol 在 吡啶 作用下， 以81.6%的产率得到4-isopropylidenecyclohexyl mesylate
  参考文献：
  名称：

  The Interaction of π Orbitals with a Carbocation over Three σ Bonds

  摘要：

  The semi-pi analogue of double hyperconjugation (''hyperconjugation/conjugation'') has been examined in 4-isopropylidenecyclohexyl mesylate (4-OMs) by comparison with the saturated analogue, trans-4-isopropylcyclohexyl mesylate(5-OMs). The unsaturated substrate reacts in 97% trifluoroethanol only four times faster than the saturated substrate. Raber-Harris plots indicate that both substrates react by k(s) mechanisms; i.e., solvolysis occurs with solvent assistance rather than carbocation formation. These results are consistent with the absence of a direct, through-bond interaction of the double bond with the reactive center. The absence is caused at least in part by less than ideal overlap of the gamma, delta pi orbitals with the alpha,beta sigma orbitals. In contrast, an electron-rich tin atom attached to the 4-position provides a large rate enhancement and changes the mechanism to carbocation formation through double hyperconjugation.

  DOI：

  10.1021/jo951643d
• 作为产物：
  描述：

  4-isopropylidenecyclohexanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以69%的产率得到4-isopropylidene-cyclohexanol
  参考文献：
  名称：

  The Interaction of π Orbitals with a Carbocation over Three σ Bonds

  摘要：

  The semi-pi analogue of double hyperconjugation (''hyperconjugation/conjugation'') has been examined in 4-isopropylidenecyclohexyl mesylate (4-OMs) by comparison with the saturated analogue, trans-4-isopropylcyclohexyl mesylate(5-OMs). The unsaturated substrate reacts in 97% trifluoroethanol only four times faster than the saturated substrate. Raber-Harris plots indicate that both substrates react by k(s) mechanisms; i.e., solvolysis occurs with solvent assistance rather than carbocation formation. These results are consistent with the absence of a direct, through-bond interaction of the double bond with the reactive center. The absence is caused at least in part by less than ideal overlap of the gamma, delta pi orbitals with the alpha,beta sigma orbitals. In contrast, an electron-rich tin atom attached to the 4-position provides a large rate enhancement and changes the mechanism to carbocation formation through double hyperconjugation.

  DOI：

  10.1021/jo951643d

文献信息

• Tasteful natural sweetener and flavor
  申请人：EPC Natural Products Co., Ltd.

  公开号：US11154079B2

  公开（公告）日：2021-10-26

  The invention describes products, uses thereof, compositions thereof, and methods to prepare products formed from Maillard reaction products from a sugar donor and/or sweet tea extracts, stevia extracts, swingle (mogroside) extracts, one or more sweet tea extract components, one or more steviol glycosides, one or more mogrosides, one or more glycosylated sweet tea glycosides, one or more glycosylated steviol glycosides or one or more glycosylated mogrosides and an amine donor/reactant.

  本发明描述了由糖供体和/或甜茶提取物、甜叶菊提取物、秋茄（mogroside）提取物、一种或多种甜茶提取物成分、一种或多种甜菊醇苷、一种或多种mogrosides、一种或多种糖基化甜茶苷、一种或多种糖基化甜菊醇苷或一种或多种糖基化mogrosides和胺供体/反应物的Maillard反应产物形成的产品、其用途、其组合物和制备方法。
• TASTEFUL NATURAL SWEETENER AND FLAVOR
  申请人：EPC Natural Products Co., Ltd.

  公开号：US20200029607A1

  公开（公告）日：2020-01-30

  The invention describes products, uses thereof, compositions thereof, and methods to prepare products formed from Maillard reaction products from a sugar donor and/or sweet tea extracts, stevia extracts, swingle (mogroside) extracts, one or more sweet tea extract components, one or more steviol glycosides, one or more mogrosides, one or more glycosylated sweet tea glycosides, one or more glycosylated steviol glycosides or one or more glycosylated mogrosides and an amine donor/reactant.
• SWEETENER AND FLAVOR COMPOSITIONS, METHODS OF MAKING AND METHODS OF USE THEREOF
  申请人：Shi Weiyao

  公开号：US20190343155A1

  公开（公告）日：2019-11-14

  Sweetener and flavor compositions with improved taste profiles are disclosed. Also disclosed are methods of making and methods of using such sweetener and flavor compositions.
• The Interaction of π Orbitals with a Carbocation over Three σ Bonds
  作者：Joseph B. Lambert、Sol M. Ciro

  DOI：10.1021/jo951643d

  日期：1996.1.1

  The semi-pi analogue of double hyperconjugation (''hyperconjugation/conjugation'') has been examined in 4-isopropylidenecyclohexyl mesylate (4-OMs) by comparison with the saturated analogue, trans-4-isopropylcyclohexyl mesylate(5-OMs). The unsaturated substrate reacts in 97% trifluoroethanol only four times faster than the saturated substrate. Raber-Harris plots indicate that both substrates react by k(s) mechanisms; i.e., solvolysis occurs with solvent assistance rather than carbocation formation. These results are consistent with the absence of a direct, through-bond interaction of the double bond with the reactive center. The absence is caused at least in part by less than ideal overlap of the gamma, delta pi orbitals with the alpha,beta sigma orbitals. In contrast, an electron-rich tin atom attached to the 4-position provides a large rate enhancement and changes the mechanism to carbocation formation through double hyperconjugation.