(+)-(1R)-2,2-Dimethyl-3-methylidenecyclopentane-1-acetaldehyde | 144342-40-5

• 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)-2,2-Dimethyl-3-methylidenecyclopentane-1-acetaldehyde
• 英文别名: (1R)-(2,2-dimethyl-3-methylidenecyclopentyl)-1-acetaldehyde；(1R)-(2,2-dimethyl-3-methylenecyclopentyl)-1-acetaldehyde；2-[(1R)-2,2-dimethyl-3-methylidenecyclopentyl]acetaldehyde
• CAS: 144342-40-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: QIMUYKYZQUADBG-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-(1R)-2,2-Dimethyl-3-methylidenecyclopentane-1-acetaldehyde 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (1R,5R)-2-Hydroxy-8,8-dimethyl-1-phenylselanylmethyl-2-azonia-bicyclo[3.2.1]oct-2-ene; bromide
  参考文献：
  名称：

  Spiro- and bridged-ring forming electrophile induced → oxime → nitrone cycloaddition cascades. Multiplication of chirality

  摘要：

  Electrophile induced 6-exo-trig spirocyclisation of oximes onto 5-, 6- or 7-membered cycloalkenes occurs stereo- and regio- specifically in good yield. Bridged - ring forming cyclisations creating bicycle-[3.3.1]- and bicyclo-[3.2.1]-ring systems also occur in good yield. Chiral bridged-ring systems have been synthesised, via the latter processes, that involve multiplication of chiral centres from one to six and seven in one pot reactions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01255-0
• 作为产物：
  描述：

  (-)-(1R)-2-(2-Iodoethyl)-6,6-dimethylbicyclo<3.1.1>hept-2-ene 在 过氧乙酸 、 lithium hydroxide 、 ethylene diamine tetraacetic acid tetrasodium salt 、 sodium carbonate 、 zinc dibromide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 (+)-(1R)-2,2-Dimethyl-3-methylidenecyclopentane-1-acetaldehyde
  参考文献：
  名称：

  制备樟脑类似物：檀香状增香剂醇的亲脂性基团†

  摘要：

  结合结构-活性关系研究，制备了樟脑类似物（（+）- 4b），它是檀香状增香剂的重要组成部分。通过将相应的α- by烯衍生物2环氧化，然后进行催化的ZnBr 2异构化（流程2），获得五元环类似物4。通过臭氧分解α-樟脑烯基乙酸酯（（-）- 14b），然后进行分子内羟醛缩合，获得六元环骨架（方案5）。给出13 C-NMR分配。

  DOI：

  10.1002/hlca.19920750507

文献信息

• X=Y–ZH Systems as potential 1,3-dipoles. Part 54: Stereo- and facially-selective formation of bridged bicyclic N-heterocycles via a sequential one-pot electrophile induced oxime→nitrone→cycloaddition sequence. Multiplication of chirality
  作者：H Ali Dondas、Ronald Grigg、Sylvie Thibault、W Anthony Thomas、Mark Thornton-Pett

  DOI：10.1016/s0040-4020(02)00564-1

  日期：2002.7

  Electrophile induced bridged-ring forming cyclisations creating azabicyclo-[3.3.1]- and azabicyclo-[3.2.1]-nitrones, followed by cycloaddition, occur stereo-, regio- and facially specifically in good to excellent yield. Chiral bridged-ring systems have been synthesised that involve multiplication of chiral centres from one to six and one to seven in one pot reactions.

  亲电试剂诱导形成桥环的桥环形成氮杂双环-[3.3.1]-和氮杂双环-[3.2.1]-亚硝基，然后环加成，特别以良好或优异的收率发生立体，区域和面部。已经合成了手性桥环系统，其涉及在一个锅反应中手性中心从一到六个和一到七个的倍增。
• N-Heterocycles from Oxime and Oxime O-Benzyl Ethers via Electrophile Induced - Ring Formation. Route to Cyclic and Bicyclic Amine and Hydroxylamine
  作者：H. Ali Dondas、Naciye Yaktubay

  DOI：10.1515/hc.2003.9.4.337

  日期：2003.1

  creating cyclic and bicyclic ring systems occur in good yield. Chiral bridged-ring systems have been prepared that involve multiplication of chiral centres from one to three in one pot reactions. Formation of chiral bicyclic bridged ring N-hydroxylamine (4) and amine (7) were prepared from aldoxime (2) and oxime Ο benzyl ether (5) respectively via phenylselenyl induced cyclisations reactions. Creating bicyclo-[3

  苯硒基和碘诱导手性和非手性环形成环化，产生桥连双环-[3.2.1] 和环环 N-羟胺和双环-[3.2.1] 环胺发生立体、区域和面部特别是涉及从一个手性中心的倍增以中等至良好的收率进行二合三合一反应。还报道了溴诱导环化和 1,3-偶极环加成产生异恶唑烷环的例子。引言： 含氮亲核试剂的烯类如胺、肼腙、亚胺异羟肟酸和肟的亲电诱导环化在文献中有很多报道，其中产物有吲哚里西啶、喹嗪、异喹啉和吲哚生物碱，具有显着的生物学作用。活动”。1,3-偶极环加成 (1, 3-DC) 硝酮与烯烃反应生成异恶唑烷是有机化学中的基本反应之一。异恶唑烷是有用的合成中间体，显示出 N-0 键易于还原裂解，生成相应的 1,3-氨基醇”。Grigg 等人最近报道了一系列亲电子诱导的肟 -> 硝酮 -> 环加成级联反应，提供硝酮并且它们的环加合物产率很高”。在最近的论文中，我们报道了苯硒基、碘和溴是用于影响立体和区域特异性螺
• Spiro- and bridged-ring forming electrophile induced → oxime → nitrone cycloaddition cascades. Multiplication of chirality
  作者：H.Ali Dondas、Ronald Grigg、Christopher S. Frampton

  DOI：10.1016/s0040-4039(97)01255-0

  日期：1997.8

  Electrophile induced 6-exo-trig spirocyclisation of oximes onto 5-, 6- or 7-membered cycloalkenes occurs stereo- and regio- specifically in good yield. Bridged - ring forming cyclisations creating bicycle-[3.3.1]- and bicyclo-[3.2.1]-ring systems also occur in good yield. Chiral bridged-ring systems have been synthesised, via the latter processes, that involve multiplication of chiral centres from one to six and seven in one pot reactions. (C) 1997 Elsevier Science Ltd.
• Preparation of Campholenal Analogues: Chirons for the lipophilic moiety of sandalwood-like odorant alcohols
  作者：Christian Chapuis、Robert Brauchli

  DOI：10.1002/hlca.19920750507

  日期：1992.8.13

  In connection with structure-activity relationship studies, analogues of campholenal ((+)-4b), an important building block for sandalwood-like odorants, were prepared. The five-membered-ring analogues 4 were obtained by epoxidation of the corresponding α-pinene derivatives 2, followed by catalytic ZnBr2 isomerisation (Scheme 2). The six-membered-ring skeleton was obtained by ozonolysis of α-campholenyl

  结合结构-活性关系研究，制备了樟脑类似物（（+）- 4b），它是檀香状增香剂的重要组成部分。通过将相应的α- by烯衍生物2环氧化，然后进行催化的ZnBr 2异构化（流程2），获得五元环类似物4。通过臭氧分解α-樟脑烯基乙酸酯（（-）- 14b），然后进行分子内羟醛缩合，获得六元环骨架（方案5）。给出13 C-NMR分配。