(1S, 2R)-2-methoxy-1-apocamphanecarboxylic acid | 125554-29-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S, 2R)-2-methoxy-1-apocamphanecarboxylic acid
• 英文别名: (1S,2R,4R)-2-methoxy-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acid
• CAS: 125554-29-2
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: YJTSVLSRPMNSHG-XLDPMVHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S, 2R)-2-methoxy-1-apocamphanecarboxylic acid 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 (4R,5R)-4-methoxy-3-(2R-methoxy-1S-apocamphane-1-carbonyl)-5-phenylselenyl-2-thiazolidinone
  参考文献：
  名称：

  Isozumi, Hirokazu; Hoshimoto, Shigeki; Matsunaga, Hirofumi, Heterocycles, 2003, vol. 59, # 1, p. 323 - 332

  摘要：

  DOI：
• 作为产物：
  描述：

  [(1R,2R,4R)-2-methoxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 碳酸氢钠 、 sodium bromide 作用下， 生成 (1S, 2R)-2-methoxy-1-apocamphanecarboxylic acid
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0

文献信息

• Highly efficient chiral 2-oxazolidinone auxiliaries derived from methylcyclopentadienes and 2-oxazolone
  作者：Noriaki Hashimoto、Tadao Ishizuka、Takehisa Kunieda

  DOI：10.1016/s0040-4039(00)75800-x

  日期：1994.1

  10-hexamethyl- and (1S, 2R, 6S, 7S, 10R)-1, 7, 8, 9, 10, 10-pentamethyl-3-oxa-5-azatricyclo[5.2.1.02,6]dec-8-en-4-ones and their enantiomers, derived from hexamethyl- and pentamethylcyclopentadienes and 2-oxazolone, serve as extremely powerful chiral auxiliaries in the asymmetric alkylations and Diels-Alder reaction.

  基于[4 + 2]环加成物的立体拥塞的2-恶唑烷酮，（1 R，2 R，6 S，7 S）-1、7、8、9、10、10-六甲基和（1 S，2 R， 6 S，7 S，10 R）-1、7、8、9、10、10-五甲基-3-氧杂-5-氮杂三环[5.2.1.0 2,6 ] dec-8-en-4-ones及其衍生自六甲基和五甲基环戊二烯和2-恶唑酮的对映异构体在不对称烷基化和Diels-Alder反应中起着极其强大的手性助剂的作用。
• An Efficient Synthesis of Thioesters Via TFA-Catalyzed Reaction of Carboxylic Acid and Thiols: Remarkably Facile C–S Bond Formation
  作者：Adel S. El-Azab、Alaa A.-M. Abdel-Aziz

  DOI：10.1080/10426507.2012.664220

  日期：2012.9.1

  Abstract A general, facile, and efficient new synthetic path to thioesters was established by employing defined TFA-catalyzed reaction of carboxylic acid and thiol under mild conditions. The structure of the newly synthesized compounds was determined by infrared spectroscopy, nuclear magnetic resonance, and a single crystal X-ray crystallographic analysis. Supplemental materials are available for this

  摘要 通过在温和条件下采用特定的三氟乙酸催化羧酸和硫醇的反应，建立了一种通用、简便、高效的硫酯合成新途径。新合成化合物的结构通过红外光谱、核磁共振和单晶 X 射线晶体学分析确定。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Highly Efficient Preparation of Both Enantiomers of Versatile Chiral Synthon for 1,2-Diamines via the Fe(III)-Catalyzed Oxidation of 2-Imidazolone
  作者：Hirofumi Matsunaga、Tadao Ishizuka、Iori Eshita、Shoichi Tsunoda、Naoko Ishimoto、Shin Ando

  DOI：10.3987/com-13-s(s)104

  日期：——

  A new method was established for the preparation of both of the enantiomers of trans-4,5-dimethoxy-2-imidazolidinone (DMIm) via the Fe(III)-catalyzed oxidation of 2-imidazolone by H2O2-urea, which allowed the subsequent achievement of optical resolution via the introduction of a MAC moiety. and a 2-mesitylenesulfonyl group at the two nitrogen positions of DMIm, which then were easily removed. The two enantiomers are useful as versatile chiral synthons for 1,2-diamines.
• Hashimoto Noriaki, Ishizuka Tadao, Kunieda Takehisa, Tetrahedron Lett, 35 (1994) N 5, S 721-724
  作者：Hashimoto Noriaki, Ishizuka Tadao, Kunieda Takehisa

  DOI：——

  日期：——