methyl (1R,2R,3S)-3-(ethylthio)-3-methyl-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate | 145213-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: methyl (1R,2R,3S)-3-(ethylthio)-3-methyl-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate
• 英文别名: (1S,2R,3R)-1-ethylthio-3-methoxycarbonyl-1-methyl-2-(oxazolidin-2-on-3-yl)carbonylcyclobutane；methyl (1R,2R,3S)-3-ethylsulfanyl-3-methyl-2-(2-oxo-1,3-oxazolidine-3-carbonyl)cyclobutane-1-carboxylate
• CAS: 145213-33-8
• 化学式: C₁₃H₁₉NO₅S
• 分子量: 301.364
• InChiKey: GGVDHQRDUNRFTH-KKFJDGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丁基1-环己烯基硫醚 、 2-(ethylthio)propene 、 methyl (1R,2R,3S)-3-(ethylthio)-3-methyl-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate 以(1R,2R,3R)-1-ethylthio-3-methoxycarbonyl-1-methyl-2-(oxazolidin-2-on-3-yl)carbonylcyclobutane (72:28, 70%) was obtained的产率得到methyl (1R,2R,3R)-3-(ethylthio)-3-methyl-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate
  参考文献：
  名称：

  Cyclobutane derivatives

  摘要：

  以下是一般式（I）所代表的环丁烷衍生物：##STR1## 其中X代表由以下公式表示的一个基团##STR2##或由以下公式表示的一个基团##STR3##，该衍生物预计可用作试剂、药物、农业化学品和香料，以及其制备的中间体。

  公开号：

  US05250697A1
• 作为产物：
  描述：

  2-(ethylthio)propene 、 3-[(E)-3-(methoxycarbonyl)-propenoyl]-oxazolidin-2-one 在 二异丙氧基二氯化钛 、 (+)-4,5-双[羟基(二苯基)甲基]-2-甲基-2-苯基-1,3-二氧戊环 作用下， 以 甲苯 、 Petroleum ether 为溶剂， 以51%的产率得到methyl (1R,2R,3S)-3-(ethylthio)-3-methyl-2-((2-oxo-1,3-oxazolidin-3-yl)carbonyl)cyclobutanecarboxylate
  参考文献：
  名称：

  Asymmetric [2 + 2] cycloaddition reaction catalyzed by a chiral titanium reagent

  摘要：

  In the presence of certain Lewis acids, alkenes containing an alkylthio group (for example, ketene dithioacetals, alkenyl sulfides, alkynyl sulfides, and allenyl sulfides) react with electron deficient olefins to give the corresponding cyclobutane, cyclobutene, or methylene cyclobutane derivatives. By employing a chiral titanium catalyst generated in situ from dichlorodiisopropoxytitanium and a tartrate-derived chiral diol, the [2 + 2] cycloaddition reaction proceeds with high enantioselectivity.

  DOI：

  10.1021/ja00049a020

文献信息

• Novel cyclobutane derivative
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP0444597A1

  公开（公告）日：1991-09-04

  This invention relates to a cyclobutane derivative represented by the following general formula (I): wherein X represents a group represented by the formula (wherein R¹ represents an alkyl group having 1 to 5 carbon atoms or an aryl-substituted alkyl group wherein the alkyl group has 1 to 5 carbon atoms; R² represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a protected hydroxyalkyl group having 1 to 5 carbon atoms or a protected carboxyl group; and R³ and R⁴ independently represent each a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a protected hydroxyalkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an aryl-substituted alkoxy group wherein the alkoxy group has 1 to 5 carbon atoms; or alternately R³ and R⁴ are bound together to thereby form a 3- to 30-membered carbocyclic or heterocyclic ring); A represents an optionally substituted polymethylene group having 2 to 5 carbon atoms; Y represents an oxygen or a sulfur atom; and Z represents an optionally substituted methylene group or an oxygen or a sulfur atom; which is expected to be useful as reagents, drugs, agricultural chemicals and perfumes as well as an intermediate for the preparation thereof.

  本发明涉及一种由以下通式 (I) 代表的环丁烷衍生物： 其中 X 代表由式（I）表示的基团 (其中 R¹ 代表具有 1 至 5 个碳原子的烷基或芳基取代的烷基，其中烷基具有 1 至 5 个碳原子； R² 代表氢原子、具有 1 至 5 个碳原子的烷基、具有 1 至 5 个碳原子的受保护羟烷基或受保护羧基；以及 R³ 和 R⁴ 各自独立地代表氢原子、具有 1 至 5 个碳原子的烷基、具有 1 至 5 个碳原子的受保护羟烷基、具有 1 至 5 个碳原子的烷氧基或芳基取代的烷氧基（其中烷氧基具有 1 至 5 个碳原子）；或 交替地将 R³ 和 R⁴ 结合在一起，从而形成 3 至 30 元的碳环或杂环）； A 代表具有 2 至 5 个碳原子的任选取代的聚亚甲基； Y 代表氧原子或硫原子；以及 Z 代表任选取代的亚甲基或氧或硫原子； 可望用作试剂、药物、农药和香料以及制备这些物质的中间体。
• US5250697A
  申请人：——

  公开号：US5250697A

  公开（公告）日：1993-10-05
• Asymmetric [2 + 2] cycloaddition reaction catalyzed by a chiral titanium reagent
  作者：Koichi Narasaka、Yujiro Hayashi、Hideshi Shimadzu、Shigeo Niihata

  DOI：10.1021/ja00049a020

  日期：1992.11

  In the presence of certain Lewis acids, alkenes containing an alkylthio group (for example, ketene dithioacetals, alkenyl sulfides, alkynyl sulfides, and allenyl sulfides) react with electron deficient olefins to give the corresponding cyclobutane, cyclobutene, or methylene cyclobutane derivatives. By employing a chiral titanium catalyst generated in situ from dichlorodiisopropoxytitanium and a tartrate-derived chiral diol, the [2 + 2] cycloaddition reaction proceeds with high enantioselectivity.
• Cyclobutane derivatives
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US05250697A1

  公开（公告）日：1993-10-05

  Cyclobutane derivatives represented by the following general formula (I): ##STR1## wherein X represents a group represented by the formula ##STR2## or the formula ##STR3## which is expected to be useful as reagents, drugs, agricultural chemicals and perfumes as well as an intermediate for the preparation thereof.

  以下是一般式（I）所代表的环丁烷衍生物：##STR1## 其中X代表由以下公式表示的一个基团##STR2##或由以下公式表示的一个基团##STR3##，该衍生物预计可用作试剂、药物、农业化学品和香料，以及其制备的中间体。