(2R,3R)-bis((tert-butyldiphenylsiloxy)methyl)cyclobutanone | 124282-18-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R)-bis((tert-butyldiphenylsiloxy)methyl)cyclobutanone
• 英文别名: (-)-(2R,3R)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclobutanone；(2R,3R)-2,3-bis[[tert-butyl(diphenyl)silyl]oxymethyl]cyclobutan-1-one
• CAS: 124282-18-4
• 化学式: C₃₈H₄₆O₃Si₂
• 分子量: 606.952
• InChiKey: GYAQQCQSTIRDJU-QGRQJHSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,3R)-2,3-bis((tert-butyldiphenylsiloxy)methyl)-1,1-bis(methylthio)cyclobutane 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以91%的产率得到(2R,3R)-bis((tert-butyldiphenylsiloxy)methyl)cyclobutanone
  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

• Asymmetric [2+2] Cycloaddition Reaction between α,β-Unsaturated Acid Derivatives and Alkynyl or Alkenyl Sulfides Catalyzed by a Chiral Titanium Reagent
  作者：Yujiro Hayashi、Koichi Narasaka

  DOI：10.1246/cl.1990.1295

  日期：1990.8

  Asymmetric [2+2] cycloaddition reaction between 3-(acryloyl)-1,3-oxazolidin-2-one derivatives and alkynyl or alkenyl sulfides proceeds by the use of a chiral titanium reagent to give the corresponding cyclobutene or cyclobutane derivatives in high enantioselectivity.

  3-(丙烯酰基)-1,3-恶唑烷-2-酮衍生物与炔基或烯基硫化物之间的不对称[2+2]环加成反应通过使用手性钛试剂进行，以高对映选择性得到相应的环丁烯或环丁烷衍生物.
• 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。
• Narasaka Koichi, Hayashi Yujiro, Shimadzu Hideshi, Niihata Shigeo, J. Amer. Chem. Soc., 114 (1992) N 23, S 8869-8885
  作者：Narasaka Koichi, Hayashi Yujiro, Shimadzu Hideshi, Niihata Shigeo

  DOI：——

  日期：——
• 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.