trimethyl(2-((RS)-2-((R)-4-methylcyclohex-3-enyl)propyl)cyclopent-1-enyloxy)silane | 1035967-93-1

• 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: trimethyl(2-((RS)-2-((R)-4-methylcyclohex-3-enyl)propyl)cyclopent-1-enyloxy)silane
• 英文别名: trimethyl-[2-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propyl]cyclopenten-1-yl]oxysilane
• CAS: 1035967-93-1
• 化学式: C₁₈H₃₂OSi
• 分子量: 292.537
• InChiKey: JLMPHSGLSVXVLD-LYKKTTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  trimethyl(2-((RS)-2-((R)-4-methylcyclohex-3-enyl)propyl)cyclopent-1-enyloxy)silane 在 正丁基锂 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以79%的产率得到nectaryl
  参考文献：
  名称：

  Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl®

  摘要：

  The fragrance Nectaryl (R) 1 was prepared by the radical addition of cyclopentanone to (+)-limonene. All the four stereoisomers of this fragrance were prepared by the enzymatic acetylation of the corresponding alcohols in good de. The absolute configurations have been unambiguously assigned by the chemical correlation and X-ray crystal structure of a dinitrobenzoate derivate. The olfactory evaluation is also reported. The odour perception is mainly related to the configuration at the stereocentre alpha to the carbonyl group. Chiral protonations of the lithium enolate or the enolester of 1 to give a diastereomeric enriched mixture of 1 are reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.011
• 作为产物：
  描述：

  三甲基氯硅烷 、 nectaryl 在 吡啶 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以90%的产率得到trimethyl(2-((RS)-2-((R)-4-methylcyclohex-3-enyl)propyl)cyclopent-1-enyloxy)silane
  参考文献：
  名称：

  Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl®

  摘要：

  The fragrance Nectaryl (R) 1 was prepared by the radical addition of cyclopentanone to (+)-limonene. All the four stereoisomers of this fragrance were prepared by the enzymatic acetylation of the corresponding alcohols in good de. The absolute configurations have been unambiguously assigned by the chemical correlation and X-ray crystal structure of a dinitrobenzoate derivate. The olfactory evaluation is also reported. The odour perception is mainly related to the configuration at the stereocentre alpha to the carbonyl group. Chiral protonations of the lithium enolate or the enolester of 1 to give a diastereomeric enriched mixture of 1 are reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.011

文献信息

• Synthesis and olfactory evaluation of all stereoisomers of the fragrance Nectaryl®
  作者：Elisabetta Brenna、Claudio Fuganti、Francesco G. Gatti、Luciana Malpezzi、Stefano Serra

  DOI：10.1016/j.tetasy.2008.03.011

  日期：2008.4

  The fragrance Nectaryl (R) 1 was prepared by the radical addition of cyclopentanone to (+)-limonene. All the four stereoisomers of this fragrance were prepared by the enzymatic acetylation of the corresponding alcohols in good de. The absolute configurations have been unambiguously assigned by the chemical correlation and X-ray crystal structure of a dinitrobenzoate derivate. The olfactory evaluation is also reported. The odour perception is mainly related to the configuration at the stereocentre alpha to the carbonyl group. Chiral protonations of the lithium enolate or the enolester of 1 to give a diastereomeric enriched mixture of 1 are reported. (C) 2008 Elsevier Ltd. All rights reserved.