(1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester | 141435-12-3

• 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: (1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester
• 英文别名: (4S,5S)-5-methoxycarbonyl-4-(oxazolidin-2-on-3-yl)carbonyl-1-cyclohexene；methyl (1S,6S)-6-(2-oxo-1,3-oxazolidine-3-carbonyl)cyclohex-3-ene-1-carboxylate
• CAS: 141435-12-3
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: MUGWLLYNEAVVIB-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester 在 palladium on activated charcoal lithium hydroxide 、 二苯基膦叠氮化物 、 氢气 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 69.5h， 生成 (1S,2S)-2-methanesulfonylaminocyclohexanecarboxylic acid
  参考文献：
  名称：

  Investigation of ligand loading and asymmetric amplification in CHAOx-catalyzed asymmetric diethylzinc additions

  摘要：

  The recently developed (cyclohexylsulfonylamino)oxazoline (CHAOx) ligand was found to provide high ee's and consistent reaction rates in the asymmetric diethylzinc addition to benzaldehyde over a remarkably large loading range of 0.05-10 mol%. Turnover numbers of 1000-2000 can be explained by the absence of a nonlinear effect and the formation of a catalytically active monomer complex. Substituents at the nitrogen donor atoms of the bidentate ligand prevent zinc-complex dimerization. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.022
• 作为产物：
  描述：

  3-[(E)-3-(methoxycarbonyl)-propenoyl]-oxazolidin-2-one 、 1,3-丁二烯 在 二异丙氧基二氯化钛 、 4 A molecular sieve 、 (+)-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 正己烷 、 甲苯 为溶剂， 反应 74.0h， 以80%的产率得到(1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Investigation of ligand loading and asymmetric amplification in CHAOx-catalyzed asymmetric diethylzinc additions

  摘要：

  The recently developed (cyclohexylsulfonylamino)oxazoline (CHAOx) ligand was found to provide high ee's and consistent reaction rates in the asymmetric diethylzinc addition to benzaldehyde over a remarkably large loading range of 0.05-10 mol%. Turnover numbers of 1000-2000 can be explained by the absence of a nonlinear effect and the formation of a catalytically active monomer complex. Substituents at the nitrogen donor atoms of the bidentate ligand prevent zinc-complex dimerization. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.022

文献信息

• Adenine and guanine derivatives for the treatment of hepatitis virus
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US05374625A1

  公开（公告）日：1994-12-20

  A novel nucleic acid derivative represented by the following general formula (I) and physiologically acceptable salt thereof which are expected to have an antiviral activity: ##STR1## wherein B represents a nucleic acid base derivative; A.sup.1 and A.sup.2 represent, independently of each other, OR.sup.1 or OCOR.sup.1 ; R.sup.1 represents a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; l represents a number of 0 or 1; and m and n each represents an integer of 0-2; provided that when l and m are 0, n is 0 or 2.

  由以下一般式（I）表示的新型核酸衍生物及其生理上可接受的盐，预计具有抗病毒活性：##STR1## 其中B代表核酸碱基衍生物；A.sup.1和A.sup.2分别表示OR.sup.1或OCOR.sup.1；R.sup.1代表氢原子、取代或未取代的烷基或取代或未取代的芳基；l表示0或1的数字；m和n分别表示0-2的整数；但当l和m为0时，n为0或2。
• Asymmetric Diels-Alder reaction catalyzed by a chiral titanium reagent
  作者：Koichi Narasaka、Nobuharu Iwasawa、Masayuki Inoue、Tohru Yamada、Masako Nakashima、Jun Sugimori

  DOI：10.1021/ja00196a045

  日期：1989.7

  Le catalyseur chiral est genere a partir de TiCl 2 (i-PrO) 2 et du (methyl-2 phenyl-2, α,α,α',α'-tetraphenyl) dioxolanne-1,3 dimethanol-4,5,chiral

  Le catalyseur chiral estgenere a partir de TiCl 2 (i-PrO) 2 et du (methyl-2 phenyl-2, α,α,α',α'-tetraphenyl) dioxolanne-1,3 dimethylethanol-4,5,chiral
• Asymmetric Diels–Alder Reaction by the Use of a Chiral Titanium Catalyst with Molecular Sieves 4A. Remarkable Solvent Effect on the Enantioselectivity
  作者：Koichi Narasaka、Masayuki Inoue、Tohru Yamada、Jun Sugimori、Nobuharu Iwasawa

  DOI：10.1246/cl.1987.2409

  日期：1987.12.5

  A remarkable effect of solvent on the enantioselectivity was observed in the asymmetric Diels–Alder reaction of 3-(2-alkenoyl)-1,3-oxazolidin-2-ones and dienes catalyzed by a chiral titanium reagent, and the Diels–Alder adducts were obtained in high enantioselectivity when alkyl-substituted benzenes were employed as the solvent.

  在手性钛试剂催化的 3-(2-烯酰基)-1,3-恶唑烷-2-酮和二烯的不对称 Diels-Alder 反应以及 Diels-Alder 加合物中观察到溶剂对对映选择性的显着影响当使用烷基取代的苯作为溶剂时，以高对映选择性获得。
• Novel nucleic acid derivatives
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP0468352A2

  公开（公告）日：1992-01-29

  A novel nucleic acid derivative represented by the following general formula (I) and physiologically acceptable salt thereof which are expected to have an antiviral activity: wherein B represents a nucleic acid base derivative; A1 and A2 represent, independently of each other, OR1 or OCOR1; R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; ℓ represents a number of 0 or 1; and m and n each represents an integer of 0-2; provided that when ℓ and m are 0, n is 0 or 2.

  由以下通式(I)代表的新型核酸衍生物及其生理上可接受的盐，有望具有抗病毒活性： 其中 B 代表核酸碱基衍生物；A1 和 A2 各自代表 OR1 或 OCOR1；R1 代表氢原子、取代或未取代的烷基或取代或未取代的芳基；ℓ 代表 0 或 1 的数字；m 和 n 各自代表 0-2 的整数；但当 ℓ 和 m 为 0 时，n 为 0 或 2。
• US5374625A
  申请人：——

  公开号：US5374625A

  公开（公告）日：1994-12-20