(1R,4S)-(+)-3-(hydroxyimino)-2-oxo-1,7,7-trimethylbicyclo[2.2.1]heptane | 5338-41-0

• 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: (1R,4S)-(+)-3-(hydroxyimino)-2-oxo-1,7,7-trimethylbicyclo[2.2.1]heptane
• 英文别名: (Z)-(1R)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one；syn-(1R)-1-camphorquinone-3-oxime；(1R)-bornane-2,3-dione-3-(Z)-oxime；(1R)-Bornan-2,3-dion-3-(Z)-oxim；(1R)-3-seqcis-Hydroxyimino-bornanon-(2)；anti-(1R)-(+)-Camphorquinone 3-oxime；(1R,3Z,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 5338-41-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: YRNPDSREMSMKIY-HAKKTOSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S)-(+)-3-(hydroxyimino)-2-oxo-1,7,7-trimethylbicyclo[2.2.1]heptane 、 羟胺 生成 (+)Campherchinon-γ-dioxim (2Z,3Z-Isomer)
  参考文献：
  名称：

  SCHOLL B.; HANSEN H. -J., HELV. CHIM. ACTA, 69,(1986) N 8, 1936-1958

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,E)-(+)-camphorquinone 3-oxime 生成 (1R,4S)-(+)-3-(hydroxyimino)-2-oxo-1,7,7-trimethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  Salmon-Legagneur, Annales de Chimie (Cachan, France), 1927, vol. <10>, # 7, p. 396

  摘要：

  DOI：

文献信息

• Asymmetric Sulfinylations of<i>N</i>-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides
  作者：Simon Ruppenthal、Reinhard Brückner

  DOI：10.1002/ejoc.201701603

  日期：2018.6.7

  Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β‐aminoalkoxide

  二乙基锌用1或2当量处理。最好是AlkMgCl或PhMgBr或1当量的AlkMgCl或PhMgBr。的Ñ振振有词锌酸盐- -丁基锂（效率较低），用于形成物种这是由二芳基sulfinylated亚砜，得到外消旋烷基芳基亚砜中的产率达到100％。二烷基锌试剂也可以通过用1或2当量的处理来活化。对映体纯的烷基镁β-氨基醇盐。当醇盐来自二烷基镁试剂和等摩尔量的N-甲基-（-）-麻黄碱时，这种方法最有效。该第二活化模式允许用二芳基亚砜将本来是二烷基锌试剂的亚磺酰基化。这样生成对映体比例高达93：7的烷基芳基亚砜，产率高达100％。
• Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Chiral<i>O</i>,<i>N</i>,<i>O</i>-tridentate Phenol Ligands Derived From Camphor
  作者：Dong-Sheng Lee、Shu-Ming Chang、Chun-Ying Ho、Ta-Jung Lu

  DOI：10.1002/chir.22543

  日期：2016.1

  Chiral O,N,O‐tridentate phenol ligands bearing a camphor backbone were found to be effective chiral catalysts for the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in high enantioselectivities (80–95% ee) at room temperature. Chirality 28:65–71, 2016. © 2015 Wiley Periodicals, Inc.

  发现带有樟脑骨架的手性O，N，O-三齿酚配体是将二乙基锌对映体选择性加成到芳族醛中的有效手性催化剂，在室温下具有很高的对映体选择性（80-95％ee）。手性28：65–71，2016。©2015 Wiley Periodicals，Inc.
• Asymmetric synthesis of N-1-(heteroaryl)ethyl-N-hydroxyureas
  作者：Mariusz J. Bosiak、Marek P. Krzemiński、Parasuraman Jaisankar、Marek Zaidlewicz

  DOI：10.1016/j.tetasy.2008.03.026

  日期：2008.5

  The asymmetric synthesis of two 5-lipoxygenase inhibitors (R)-N-1-(benzofuran-2-yl)ethyl-N-hydroxyurea, 99% ee, and (R)-N-1-(benzo[b]thiophen-2-yl)ethyl-N-hydroxyurea, 95% ee, is described. The enantioselective reduction of 1-(benzofuran-2-yl)ethanone oxime O-benzyl ether and 1-(benzo[b]thiophen-2-yl)ethanone oxime O-benzyl ether with borane oxazaborolidine, generated from (1R,2S,3R,4S)-3-amino-1,7

  两种5-脂氧合酶抑制剂（R）-N -1-（苯并呋喃-2-基）乙基-N-羟基脲，99％ee和（R）-N -1-（苯并[ b ]噻吩-描述了95％ee的2-基）乙基-N-羟基脲。用（1 R，2）生成的硼烷恶唑硼烷将对（1-苯并呋喃-2-基）乙酮肟O-苄基醚和1-（苯并[ b ]噻吩-2-基）乙酮肟O-苄基醚进行对映选择性还原硫，3 R，4 S）-3-氨基-1,7,7-三甲基双环[2.2.1]庚-2-醇被用于形成立体异构中心。
• Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes
  作者：Craig D. Campbell、Carmen Concellón、Andrew D. Smith

  DOI：10.1016/j.tetasy.2011.04.001

  日期：2011.4

  The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs. (C) 2011 Elsevier Ltd. All rights reserved.
• Forster, Journal of the Chemical Society, 1915, vol. 107, p. 267
  作者：Forster

  DOI：——

  日期：——