2-cyclobutylbenzo[d]oxazole | 175611-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-cyclobutylbenzo[d]oxazole
• 英文别名: 2-Cyclobutyl-1,3-benzoxazole；2-cyclobutyl-1,3-benzoxazole
• CAS: 175611-02-6
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: KHSRNAVGMWOFHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyclobutylbenzo[d]oxazole 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 trans-3-(benz-1,3-oxazol-2-yl)cyclobut-1-yl-4-nitrobenzoate
  参考文献：
  名称：

  Microbial hydroxylation of 2-cycloalkylbenoxazoles. Part II. Determination of product structures and enhancement of enantiomeric excess

  摘要：

  The determinations of product structures obtained in the microbial hydroxylations of various 2-cycloalkyl-1, 3-benzoxazoles using Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32 are described. The initially low e.e. of 3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-ol 6, 2-(benz-1, 3-oxazol-2-yl)cyclohexan-1-ol 14 and 4-(2-bent-1, 3-oxazol-2-yl)cycloheptan-1-ol 21 can be enhanced to 98% using lipase catalyzed resolution.

  DOI：

  10.1016/0957-4166(96)00031-6
• 作为产物：
  描述：

  在 水 、 caesium carbonate 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以22.8 mg的产率得到2-cyclobutylbenzo[d]oxazole
  参考文献：
  名称：

  通过Tf2O活化的酰胺实现苯并恶唑的无过渡金属烷基化/芳基化

  摘要：

  通过使用Tf 2 O活化酰胺作为烷基化/芳基化试剂，开发了一种无过渡金属的苯并恶唑烷基化/芳基化方法。温和的反应条件，尤其是对空气和水的不敏感性，进一步提高了药物合成的合成潜力。

  DOI：

  10.1002/adsc.201901078

文献信息

• Silver catalyzed decarboxylative direct C2-alkylation of benzothiazoles with carboxylic acids
  作者：Wei-Ming Zhao、Xiao-Lan Chen、Jin-Wei Yuan、Ling-Bo Qu、Li-Kun Duan、Yu-Fen Zhao

  DOI：10.1039/c3cc48069k

  日期：——

  A novel and efficient silver catalyzed decarboxylative direct C2-alkylation of benzothiazoles with carboxylic acids for the synthesis of 2-alkyl benzothiazoles was developed.

  开发了一种新颖且高效的银催化脱羧直接C2烷基化苯并噻唑与羧酸的反应，用于合成2-烷基苯并噻唑。
• Copper-Catalyzed Alkylation of Benzoxazoles with Secondary Alkyl Halides
  作者：Peng Ren、Isuf Salihu、Rosario Scopelliti、Xile Hu

  DOI：10.1021/ol300348w

  日期：2012.4.6

  Copper-catalyzed direct alkylation of benzoxazoles using nonactivated secondary alkyl halides has been developed. The best catalyst is a new copper(I) complex (1), and the reactions are promoted by bis[2-(N,N-dimethylamino)ethyl] ether.

  已经开发了使用未活化的仲烷基卤化物的铜催化的苯并恶唑的直接烷基化。最好的催化剂是新的铜（I）配合物（1），双[2-（N，N-二甲基氨基）乙基]醚可促进反应。
• Stereoselective CH Borylations of Cyclopropanes and Cyclobutanes with Silica-Supported Monophosphane-Ir Catalysts
  作者：Ryo Murakami、Kiyoshi Tsunoda、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1002/chem.201404362

  日期：2014.10.6

  Heteroatom‐directed CH borylation of cyclopropanes and cyclobutanes was achieved with silica‐supported monophosphane–Ir catalysts. Borylation occurred at the CH bonds located γ to the directing N or O atoms with exceptional cis stereoselectivity relative to the directing groups. This protocol was applied to the borylation of a tertiary CH bond of a ring‐fused cyclopropane.

  杂原子-定向Ç  ħ环丙烷和环丁烷用二氧化硅负载monophosphane-IR催化剂实现的硼基化。硼化发生在C 位于H键γ到具有卓越的定向N或O原子的顺式相对于所述定位基团的立体选择性。该协议被加到叔C的硼化一个稠环环丙烷的H键。
• Microbial hydroxylation of 2-cycloalkylbenzoxazoles. Part I. Product spectrum obtained from Cunninghamella blakesleeana DSM 1906 and Bacillus megaterium DSM 32
  作者：A. de Raadt、H. Griengl、M. Petsch、P. Plachota、N. Schoo、H. Weber、G. Braunegg、I. Kopper、M. Kreiner、A. Zeiser、K. Kieslich

  DOI：10.1016/0957-4166(96)00030-4

  日期：1996.2

  2-Cycloalkyl-1, 3-benzoxazoles and -thiazoles (ring sizes C-3 to C-8) were biotransformed using the title microorganisms. Products of preparative importance were (1S, 3S)-3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-ol 6, (1R)-3-(benz-1, 3-oxazol-2-yl)cyclopentan-1-one 8, (1R, 2R)-2-(benz-1, 3-oxazol-2-yl)cyclohexan-1-ol 14 and the corresponding cycloheptanol and cycloheptanone derivatives.
• [EN] NOVEL TRPV3 MODULATORS<br/>[FR] NOUVEAUX MODULATEURS DE TRPV3
  申请人：ABBVIE INC

  公开号：WO2013062966A2

  公开（公告）日：2013-05-02

  Disclosed herein are modulators of TRPV3 of formula (II): wherein G1, X1, X2, X3, X4, X5, G2, Ra, Rb, and u are as defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also presented.