(E)-12-Methyl-oxacyclododec-8-en-2-one | 107109-03-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (E)-12-Methyl-oxacyclododec-8-en-2-one
• 英文别名: (8E)-12-methyl-1-oxacyclododec-8-en-2-one
• CAS: 107109-03-5
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: KDEOIGPWVGHSBQ-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-tetrahydropyranyloxy-1-bromobutane 在 copper diacetate 、 iron(II) sulfate 作用下， 以 甲醇 为溶剂， 生成 (E)-12-Methyl-oxacyclododec-8-en-2-one
  参考文献：
  名称：

  铁/铜促进α-烷氧基氢过氧化物的裂解反应：区域和立体控制形成含烯烃的大环内酯

  摘要：

  报道了铁/铜介导的氢过氧化物裂解反应的几个新实例。烯烃形成的区域和立体化学符合考虑到自由基中间产物和潜在烯烃产物的优选构象的模型。结合基团选择性过氧缩酮化反应，已经实现了几种含烯烃的大环内酯类的立体控制合成。

  DOI：

  10.1016/s0040-4020(01)90584-8

文献信息

• Using stereoretention for the synthesis of <i>E</i>-macrocycles with ruthenium-based olefin metathesis catalysts
  作者：Tonia S. Ahmed、T. Patrick Montgomery、Robert H. Grubbs

  DOI：10.1039/c8sc00435h

  日期：——

  The synthesis of E-macrocycles is achieved using stereoretentive, Ru-based olefin metathesis catalysts supported by dithiolate ligands. Kinetic studies elucidate marked differences in activity among the catalysts tested, with catalyst 4 providing meaningful yields of products in much shorter reaction times than stereoretentive catalysts 2 and 3. Macrocycles were generated with excellent selectivity

  E-大环的合成是使用二硫醇盐配体负载的立体保持性，Ru基烯烃复分解催化剂来实现的。动力学研究阐明了所测试的催化剂之间活性的显着差异，其中催化剂4在比立体保持催化剂2和3短得多的反应时间内提供了有意义的产物收率。大环以优异的选择性（> 99％E）和中等至高收率（47-80％收率）从带有两种E-构型烯烃的二烯原料中生成。构建了各种环，范围从12到18元的大环化合物，包括抗生素回收苯环内酯。
• Using stereoretention for the stereoselective formation of e-macrocycles with Ru-based olefin metathesis catalysts
  申请人：California Institute of Technology

  公开号：US11407726B2

  公开（公告）日：2022-08-09

  This invention relates generally to the synthesis of E-macrocycles using stereoretentive ruthenium olefin metathesis catalysts supported by dithioiate ligands. Macrocycles were generated with excellent selectivity (>99% E) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield) from diene starting materials bearing two E-olefins or bearing one E-olefin and one terminal olefin, A variety of rings were constructed, ranging from 12- to 18-membered macrocycles, including the antibiotic recifeiolide. The invention has utility in the fields of organometallics and organic synthesis.

  本发明一般涉及使用二硫代配体支持的立体结构钌烯烃偏析催化剂合成 E-大环。从含有两个 E-烯烃或含有一个 E-烯烃和一个末端烯烃的二烯起始材料生成的大环具有极佳的选择性（>99% E）和中等至高/良好的收率（收率为 47% 至 80%；收率为 58% 至 80%）。本发明可用于有机金属和有机合成领域。
• SCHREIBER S. L.; HULIN B.; LIEW WAI-FONG, TETRAHEDRON, 42,(1986) N 11, 2945-2950
  作者：SCHREIBER S. L.、 HULIN B.、 LIEW WAI-FONG

  DOI：——

  日期：——
• USING STEREORETENTION FOR THE STEREOSELECTIVE FORMATION OF E-MACROCYCLES WITH RU-BASED OLEFIN METATHESIS CATALYSTS
  申请人：California Institute of Technology

  公开号：US20200385360A1

  公开（公告）日：2020-12-10

  This invention relates generally to the synthesis of E-macrocycles using stereoretentive ruthenium olefin metathesis catalysts supported by dithioiate ligands. Macrocycles were generated with excellent selectivity (>99% E) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield) from diene starting materials bearing two E-olefins or bearing one E-olefin and one terminal olefin, A variety of rings were constructed, ranging from 12- to 18-membered macrocycles, including the antibiotic recifeiolide. The invention has utility in the fields of organometallics and organic synthesis.
• US5936100A
  申请人：——

  公开号：US5936100A

  公开（公告）日：1999-08-10