methyl 2-(1-hydroxyethyl)pent-4-enoate | 134692-51-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2-(1-hydroxyethyl)pent-4-enoate
• 英文别名: 5-hydroxy-4-methoxycarbonylhex-1-ene；methyl 2-allyl-3-hydroxybutanoate
• CAS: 134692-51-6
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: YGJTWICMMTYPFS-UHFFFAOYSA-N

物化性质

• 沸点：
  231.0±20.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(1-hydroxyethyl)pent-4-enoate 在 CoCl₂ 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 [5-(1-chloroethyl)-6-oxooxan-3-yl] acetate
  参考文献：
  名称：

  氯化钴（II）催化的酰基卤醚裂解：范围和机理

  摘要：

  乙腈中的氯化钴（II）在温和的条件下催化多种醚与酰基卤的裂解，从而以高收率得到相应的酯。无环脂族醚裂解成相应的酯和氯化物，而环脂族醚产生ω-氯代酯。苄基醚可与苄基氯和苄基乙酰胺一起形成相应的酯。烯丙基和苄基醚裂解的比较研究表明，苄基醚可以在烯丙基醚存在下选择性裂解。可以以高度区域选择性的方式将环氧乙烷酮裂解为相应的β-氯代酯。乙烯基醚经历sp 2在这些条件下的-杂化的碳-氧键裂解。基于产物分析，讨论了涉及电子转移，随后进行O-酰化以及氯离子对S N 1或S N 2的攻击的机理。

  DOI：

  10.1016/s0040-4020(01)96041-7
• 作为产物：
  描述：

  乙酰乙酸甲酯 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 9.25h， 生成 methyl 2-(1-hydroxyethyl)pent-4-enoate
  参考文献：
  名称：

  Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System

  摘要：

  A novel catalytic system using I-2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

  DOI：

  10.1021/acs.orglett.5b01797

文献信息

• Optically active compounds having plural chiral centers and the production thereof
  申请人：Chisso Corporation

  公开号：EP0428392A2

  公开（公告）日：1991-05-22

  Optically active compounds, having a plurality of chiral centres, have the general formulae: or in which R', R2 and R4 are the same or are different and each is an alkyl, alkenyl or alkynyl group having up to 40 carbon atoms, the carbon chain of which may contain one or more of halogen, cyano, oxygen, nitrogen, silicon, sulfur and substituted or unsubstituted benzene, cyclohexane, pyridine, pyrimidine, pyridazine, pyrazine, dioxane or bicyclooctane ring 5; R3 is an alkyl, alkenyl or alkynyl groups having 3 to 40 carbon atoms ; X is hydrogen or an alkanoyl group having 2 to 40 carbon atoms; and the carbon atom with the sign, *, is an asymmetic carbon.

  具有多个手性中心的光学活性化合物的通式为 或 其中 R'、R2 和 R4 相同或不同，且各自为具有多达 40 个碳原子的烷基、烯基或炔基，其碳链可包含一个或多个卤素、氰基、氧、氮、硅、硫和取代或未取代的苯、环己烷、吡啶、嘧啶、哒嗪、吡嗪、二氧杂环或双环辛烷环 5； R3 是具有 3 至 40 个碳原子的烷基、烯基或炔基； X 是氢或具有 2 至 40 个碳原子的烷酰基； 符号 * 的碳原子为异构碳。
• Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism
  作者：Javed Iqbal、Rajiv Ranjan Srivastava

  DOI：10.1021/jo00033a020

  日期：1992.3

  Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield. Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones. Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate. The beta-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting beta-acetoxy carbonyl compound is observed. A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene. A mechanism for these acylations is proposed by invoking an electron-transfer process.
• NAKAMURA, KAORU;MIYAI, TAKEHIKO;NAGAR, ASHISH;OKA, SHINZABURO;OHNO, ATSUY+, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1179-1187
  作者：NAKAMURA, KAORU、MIYAI, TAKEHIKO、NAGAR, ASHISH、OKA, SHINZABURO、OHNO, ATSUY+

  DOI：——

  日期：——
• Processes for the preparation of optically active compounds having plural chiral centers
  申请人：Chisso Corporation

  公开号：EP0428392B1

  公开（公告）日：1998-05-27
• US5348870A
  申请人：——

  公开号：US5348870A

  公开（公告）日：1994-09-20