3-benzoyl-2,2-dimethylthiazolidine-4R-carboxylic acid | 57704-00-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-benzoyl-2,2-dimethylthiazolidine-4R-carboxylic acid
• 英文别名: (R)-3-benzoyl-2,2-dimethyl-thiazolidine-4-carboxylic acid；N-benzoyl-N,S-isopropylidene-L-cysteine；(4R)-3-Benzoyl-2,2-dimethyl-1,3-thiazolidine-4-carboxylic acid；(4R)-3-benzoyl-2,2-dimethyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 57704-00-4
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: ZTNRUDZRCMWXPD-JTQLQIEISA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  468.8±45.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2,2-dimethylthiazolidine-4R-carboxylic acid 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 32.0h， 生成 (4R)-3-benzoyl-5t-benzoyloxy-2,2-dimethyl-thiazolidine-4r-carboxylic acid methyl ester
  参考文献：
  名称：

  Iwakawa,M. et al., Canadian Journal of Chemistry, 1978, vol. 56, p. 326 - 335

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2,2-二甲基 4-噻唑烷羧酸盐酸盐 、 苯甲酰氯 在 吡啶 作用下， 以86%的产率得到3-benzoyl-2,2-dimethylthiazolidine-4R-carboxylic acid
  参考文献：
  名称：

  Memory of Chirality in the Electrochemical Oxidation of Thiazolidine-4-carboxylic Acid Derivatives

  摘要：

  Memory of chirality in the electrochemical oxidation of thiazolidine-4-carboxylic acid derivatives was observed. The relatively larger size of sulphur atom than the oxygen atom for oxazolidine-4-carboxylic acid derivative may slightly improved the enantioselectivities of the oxidized products. The bulkier penicillamine derivative 1c furnished 2c with much better enantioselectivity (91% ee) than that of the cysteine derivative 2b (85% ee). The presence of two extra dimethyl groups, for the penicillamine derivative improved the enantioselectivities of the thiazolidine derivatives from 85% ee to 91% ee.

  DOI：

  10.3987/com-09-s(s)101

文献信息

• Electroytic Partial Fluorination of Organic Compounds. 52.¹ Regio- and Diastereoselective Anodic Fluorination of Thiazolidines
  作者：Daisuke Baba、Hideki Ishii、Seiichiro Higashiya、Kiyoshi Fujisawa、Toshio Fuchigami

  DOI：10.1021/jo010472b

  日期：2001.10.1

  supporting fluoride salts. The diastereoselectivitiy of the fluorination was greatly affected by the bulkyness of the subsitituent on the nitrogen atom, and N-benzoylthiazolidine gave much higher diastereoselectivity compared with N-formyl derivative. The fluorination of the thiazolidines was not achieved by commercially available fluorinating reagents such as N-fluoropyridinium salts.

  衍生自L-半胱氨酸的N-苯甲酰基，N-乙酰乙基和N-甲酰基噻唑烷的阳极氟化反应是在二甲氧基乙烷（DME）和含有各种支持氟化物盐的乙腈中使用未分格的电池进行的。高度区域选择性氟化继续以高产率在DME中提供相应的5-单氟化噻唑烷衍生物，并且非对映选择性是中等到较高的，而与支持的氟化物盐无关。氟的非对映选择性受氮原子上取代基的庞大度极大地影响，并且与N-甲酰基衍生物相比，N-苯甲酰基噻唑烷具有更高的非对映选择性。噻唑烷的氟化不能通过市售的氟化试剂如N-氟吡啶鎓盐来实现。
• Method and apparatus for the manufacture of cosmetic solutions using ultraviolet light and electrolysis
  申请人：Anthony Michael Mark

  公开号：US10266953B1

  公开（公告）日：2019-04-23

  The invention relates to the manufacture of cosmetic solutions for use on human hair using the effects of UV light and electrolysis. In particular, a specialized cross-linking of Hydrochloride protected thiols to form protected Thiazolidines is disclosed. The process uses both UV light and electrolysis to form stable cosmetic solutions that have a variety of uses.

  本发明涉及利用紫外线和电解作用制造用于人类头发的化妆品溶液。特别是，本发明公开了一种盐酸保护硫醇形成保护噻唑烷的特殊交联方法。该工艺利用紫外线和电解形成稳定的化妆品溶液，具有多种用途。
• Asymmetric synthesis of monocyclic β-lactams from l-cysteine using photochemistry
  作者：Xiao Lu、Timothy E. Long

  DOI：10.1016/j.tetlet.2011.07.085

  日期：2011.9

  An asymmetric method to synthesize cis-configured beta-lactams using photochemistry has been developed. Aerobic photo-oxidation of L-cysteine-derived thiazolidine hydroxamate esters afforded C-3 hydroxylated products which when cyclized and deprotected gave the corresponding N-protio monocyclic beta-lactams. Published by Elsevier Ltd.
• Stereospecific synthesis of penicillins. Conversion from a peptide precursor
  作者：Jack E. Baldwin、Michael A. Christie、Stephen B. Haber、Lawrence I. Kruse

  DOI：10.1021/ja00426a077

  日期：1976.5
• Stereospecific conversion of peptides into .beta.-lactams
  作者：Jack E. Baldwin、Andrew Au、Michael Christie、Stephen B. Haber、David Hesson

  DOI：10.1021/ja00853a075

  日期：1975.10