S-methyl 2-cyanothiopropionate | 107427-81-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: S-methyl 2-cyanothiopropionate
• 英文别名: Propanethioic acid, 2-cyano-, S-methyl ester；S-methyl 2-cyanopropanethioate
• CAS: 107427-81-6
• 化学式: C₅H₇NOS
• 分子量: 129.183
• InChiKey: BJTPIIQTIDHLKO-UHFFFAOYSA-N

物化性质

• 沸点：
  214.1±23.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-methyl 2-cyanothiopropionate 在 N-[3,5-双(三氟甲基)苯基]-N′-[(9R)-6′-甲氧基-9-金鸡宁]硫脲 溶剂黄146 、 锌 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 18.0h， 生成 S-methyl (2S)-2,4-dicyano-2-methylbutanethioate
  参考文献：
  名称：

  Control of Diastereoselectivity in Tandem Asymmetric Reactions Generating Nonadjacent Stereocenters with Bifunctional Catalysis by Cinchona Alkaloids

  摘要：

  We report the manipulation of hydrogen-bonding-based cooperative catalysis to control the diastereoselectivity for a tandem asymmetric reaction creating two nonadjacent stereocenters. This ability to control both the enantioselectivity and diastereoselectivity allows, for the first time, the direct and stereoselective construction of 1,3-tertiary-quaternary stereocenters in any of the possible four configurations from the same prochiral precursors with catalytic control. The synthetic consequence of such catalyst-controlled construction of nonadjacent stereocenters is illustrated by the asymmetric synthesis of manzacidin C by using the same reaction sequence that was previously applied to the total synthesis of manzacidin A.

  DOI：

  10.1021/ja0670409
• 作为产物：
  描述：

  荒酸二甲酯 、 丙腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以45%的产率得到S-methyl 2-cyanothiopropionate
  参考文献：
  名称：

  Yokoyama, Masataka; Hatanaka, Hidekatsu; Sasaki, Atsuhi, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1187 - 1196

  摘要：

  DOI：

文献信息

• Dual-Function Cinchona Alkaloid Catalysis:  Catalytic Asymmetric Tandem Conjugate Addition−Protonation for the Direct Creation of Nonadjacent Stereocenters
  作者：Yi Wang、Xiaofeng Liu、Li Deng

  DOI：10.1021/ja060312n

  日期：2006.3.1

  addition-protonation with efficient catalytic control of two nonadjacent stereocenters. As demonstrated in a concise and highly stereoselective formal total synthesis of (-)-manzacidin A, this asymmetric tandem reaction establishes a new and versatile catalytic approach for the enantioselective and diastereoselective creation of 1,3-tertiary-quaternary stereocenters.

  催化串联不对称反应构成了直接从非手性前体在非环状分子中不对称构建非相邻立体中心的有力策略。在这篇通讯中，我们报告了在双功能金鸡纳生物碱催化剂的催化下，三取代的碳供体对 2-氯丙烯腈的高度对映选择性和非对映选择性加成。这代表了第一个不对称串联共轭加成-质子化，对两个不相邻的立体中心进行有效的催化控制。正如 (-)-manzacin A 的简洁且高度立体选择性的正式全合成所证明的那样，这种不对称串联反应为 1,3-叔-四元立体中心的对映选择性和非对映选择性创建建立了一种新的通用催化方法。
• Yokoyama, Masataka; Hatanaka, Hidekatsu; Sasaki, Atsuhi, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1187 - 1196
  作者：Yokoyama, Masataka、Hatanaka, Hidekatsu、Sasaki, Atsuhi、Shiraishi, Tadashi、Kumata, Katsushi、et al.

  DOI：——

  日期：——
• Control of Diastereoselectivity in Tandem Asymmetric Reactions Generating Nonadjacent Stereocenters with Bifunctional Catalysis by Cinchona Alkaloids
  作者：Baomin Wang、Fanghui Wu、Yi Wang、Xiaofeng Liu、Li Deng

  DOI：10.1021/ja0670409

  日期：2007.1.1

  We report the manipulation of hydrogen-bonding-based cooperative catalysis to control the diastereoselectivity for a tandem asymmetric reaction creating two nonadjacent stereocenters. This ability to control both the enantioselectivity and diastereoselectivity allows, for the first time, the direct and stereoselective construction of 1,3-tertiary-quaternary stereocenters in any of the possible four configurations from the same prochiral precursors with catalytic control. The synthetic consequence of such catalyst-controlled construction of nonadjacent stereocenters is illustrated by the asymmetric synthesis of manzacidin C by using the same reaction sequence that was previously applied to the total synthesis of manzacidin A.