ethyl (2E)-2-methylhexadec-2-enoate | 478690-77-6

• 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: ethyl (2E)-2-methylhexadec-2-enoate
• 英文别名: ethyl (E)-2-methylhexadec-2-enoate
• CAS: 478690-77-6
• 化学式: C₁₉H₃₆O₂
• 分子量: 296.494
• InChiKey: HOFJBFSOHFLKCF-ISLYRVAYSA-N

物化性质

• 沸点：
  371.9±11.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (2E)-2-methylhexadec-2-enoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以84%的产率得到methyl-hexadecenoic acid
  参考文献：
  名称：

  使用Appel试剂（PPh 3 / CBr 4）从Baylis-Hillman加合物温和而实用的立体选择性合成（Z）-和（E）-烯丙基溴：轻度合成C和E的简便方法

  摘要：

  在室温下，Appel试剂（PPh 3 / CBr 4）已用于从Baylis-Hillman加合物中高产率地立体选择性合成（Z）-和（E）-烯丙基溴。该方法已用于合成天然存在的生物活性脂肪酸酰胺，半乳糖C和E。

  DOI：

  10.1016/j.tetlet.2009.02.132
• 作为产物：
  描述：

  ethyl (Z)-2-(bromomethyl)hexadec-2-enoate 在 锌 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到ethyl (2E)-2-methylhexadec-2-enoate
  参考文献：
  名称：

  使用Appel试剂（PPh 3 / CBr 4）从Baylis-Hillman加合物温和而实用的立体选择性合成（Z）-和（E）-烯丙基溴：轻度合成C和E的简便方法

  摘要：

  在室温下，Appel试剂（PPh 3 / CBr 4）已用于从Baylis-Hillman加合物中高产率地立体选择性合成（Z）-和（E）-烯丙基溴。该方法已用于合成天然存在的生物活性脂肪酸酰胺，半乳糖C和E。

  DOI：

  10.1016/j.tetlet.2009.02.132

文献信息

• Formal Total Synthesis of Stevastelins B and B3
  作者：Jhillu Singh Yadav、Satadru Sekhar Mandal、Pabbaraja Srihari

  DOI：10.1002/hlca.201300255

  日期：2014.5

  The formal total synthesis of stevastelins B and B3 (2 and 4, resp.) have been accomplished employing a highly enantiomerically controlled Lewis acid catalyzed non‐aldol approach to obtain the syn aldol product and temperature controlled hydroboration oxidation reaction to construct four consecutive stereogenic centers. The other key reactions include Sharpless asymmetric epoxidation, macrolactonization

  Stevastelins B和B3的正式全合成（分别为2和4）已通过高度对映体控制的Lewis酸催化的非羟醛方法完成，获得了顺式羟醛产物和温控的硼氢化氧化反应，以构建四个连续的立体异构中心。其他关键反应包括Sharpless不对称环氧化，大内酯化和大内酰胺化，以构建核心骨架2和4。
• Detection of short-chain aldehydes in marine organisms: the diatom Thalassiosira rotula
  作者：Giuliana d'Ippolito、Olimpia Iadicicco、Giovanna Romano、Angelo Fontana

  DOI：10.1016/s0040-4039(02)01283-2

  日期：2002.8

  Short-chain aldehydes are analysed by GC-MS and NMR after their transformation into the corresponding carboxyethylethylidene (CET) derivatives via Wittig reaction. The procedure implies the treatment of the aldehyde with (carbetoxyethylidene)-triphenylphosphorane under very mild conditions. The method is suitable for the detection of short and medium chain aldehydes. CET derivatives are easily prepared and can be Utilised for the analysis of raw biological samples. The efficacy of the method has been tested in the identification of biologically active aldehydes in the marine diatom Thalassiosira rotula. At least two compounds, trans,trans-octadienal and 2-trans-4-trans-2,4,7-octatrienal, that have not been revealed in previous papers are unambiguously identified in the microalga. (C) 2002 Published by Elsevier Science Ltd.
• Synthesis of 1-Deoxysphingosine Derivatives with Conformationally Restricted Pyrrolidinediol Head Groups
  作者：Ann M. Dougherty、Frank E. McDonald、Dennis C. Liotta、Steven J. Moody、David C. Pallas、Carrie D. Pack、Alfred H. Merrill

  DOI：10.1021/ol052839v

  日期：2006.2.1

  A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation.