α-lithiomethyl p-tolyl sulfoxide | 51651-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-lithiomethyl p-tolyl sulfoxide
• CAS: 51651-66-2
• 化学式: C₈H₉LiOS
• 分子量: 160.166
• InChiKey: PYOFUUQYGQFIQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-lithiomethyl p-tolyl sulfoxide 生成 (S)-(-)-甲基对甲苯亚砜
  参考文献：
  名称：

  KUNIEDA, NORIO;NAKANISHI, TAKESHI;KINOSHITA, MASAYOSHI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2229-2234

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基对甲苯亚砜 、 lithium diethylamide 生成 α-lithiomethyl p-tolyl sulfoxide
  参考文献：
  名称：

  KUNIEDA, NORIO;NAKANISHI, TAKESHI;KINOSHITA, MASAYOSHI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2229-2234

  摘要：

  DOI：

文献信息

• The Preparation of Optically Active β-Keto Sulfoxides by Means of an Enantiomer-differentiating Reaction of α-Lithio Aryl Methyl Sulfoxides with Chiral Carboxylates
  作者：Norio Kunieda、Akira Suzuki、Masayoshi Kinoshita

  DOI：10.1246/bcsj.54.1143

  日期：1981.4

  The reaction of α-lithio aryl methyl sulfoxides with a limited amount of chiral carboxylates (R2–CO–O–R*) was found to be an enantiomer-differentiating reaction, affording the corresponding optically active β-keto sulfoxides (3), together with optically active aryl methyl sulfoxides which have the opposite configuration. The optical purity and the predominant configuration of 3 obtained were assigned

  发现 α-锂硫芳基甲基亚砜与有限量的手性羧酸盐 (R2-CO-O-R*) 的反应是对映异构体区分反应，提供相应的光学活性 β-酮亚砜 (3)，一起具有相反构型的旋光芳基甲基亚砜。获得的 3 的光学纯度和主要构型通过极化分析和 NMR 的组合指定。该反应的对映选择性程度受酯部分 R2 的性质影响，表明光学产率从 1.3%（其中 R2 为乙基（3b））增加到 70.3%，其中 R2 为叔丁基（3f） . 通过考虑六元环过渡态讨论了反应的立体化学过程。此外，
• Efficient synthesis of 4,4-disubstituted-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxides
  作者：Esteban Domı́nguez、Jesús de Blas、Miriam del Prado、M.Teresa Aranda、M.Carmen Carreño、José L. Garcı́a Ruano

  DOI：10.1016/s0040-4039(00)01779-2

  日期：2000.12

  A simple method for the preparation of 4,4-disubstituted-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxides is described. Treatment of N-sulfonyl ketimines 2 and 3 with different carbon nucleophiles afforded the corresponding of 4,4-disubstituted-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxides 1 in isolated yields of 35–84%.

  描述了一种制备4,4-二取代-3,4-二氢-1 H -2,1,3-苯并噻二嗪2,2-二氧化物的简单方法。用不同的碳亲核试剂处理N-磺酰基酮亚胺2和3得到相应的4,4-二取代-3,4-二氢-1 H -2,1,3-苯并噻二嗪2,2-二氧化物1的分离产率为35 –84％。
• Stereoselective synthesis of 3-p-tolylsulphinyl-4-aryl-β-lactams
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano、Sergio Thea

  DOI：10.1039/c39840000861

  日期：——

  3-p-Tolylsulphinyl-4-aryl-β-lactams (4) have been synthesised in moderate yield and with good overall stereoselectivity by the condensation of aryl aldimines with derivatives of 2-p-tolylsulphinylacetic acid (2).

  3- p -Tolylsulphinyl -4-芳-β内酰胺（4）已在适中的产率和与由芳基醛亚胺与2-衍生物缩合良好的整体立体选择性合成了p -tolylsulphinylacetic酸（2）。
• A short enantiodivergent synthesis of d-erythro and l-threo sphingosine
  作者：Noureddine Khiar、Kamaljit Singh、Mercedes García、Manuel Martín-Lomas

  DOI：10.1016/s0040-4039(99)01112-0

  日期：1999.7

  A new, short (6 steps) and efficient enantiodivergent route to both D-erythro and L threo-sphingosine I and II is disclosed. The high diastereoselection (100% de) reached in the creation of the C-3 stereocenter relies on the use of a sulfoxide as chiral controlling agent in the reduction of the common precursor beta-keto sulfoxide 3. The desired E-alkene of sphingosines has been constructed by the Schlosser modification of the Wittig reaction between aldehyde 8 and the phosphoniun salt 9. The reported methodology can easily be extended to the synthesis of a large number of optically pure syn and anti amino alcohols starting from commercially available amino acids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of polyhydroxylated natural products II. The C-1/C-12 unit of amphotericin B.
  作者：Guy Solladie、Jean Hutt

  DOI：10.1016/s0040-4039(01)80992-8

  日期：1987.1