(R)-5-(chloromethyl)-2,5-diphenyl-4,5-dihydrooxazole | 1286255-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-5-(chloromethyl)-2,5-diphenyl-4,5-dihydrooxazole
• 英文别名: (R)-5-methyl-2,5-diphenyl-4,5-dihydrooxazole；(5R)-5-(chloromethyl)-2,5-diphenyl-4H-1,3-oxazole
• CAS: 1286255-42-2
• 化学式: C₁₆H₁₄ClNO
• 分子量: 271.746
• InChiKey: VZEZCHJJGNGZNC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-phenylallyl)benzamide 在 chloramine T trihydrate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以85%的产率得到(R)-5-(chloromethyl)-2,5-diphenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  氯磺酰胺盐是不饱和酰胺的有机催化不对称氯环化的优良亲电子氯前体

  摘要：

  在烯烃的有机催化不对称氯官能化中，氯胺-T·3H 2 O和其他氯磺酰胺盐可作为易得，稳定且廉价的亲电子氯的前体。与可商购的有机催化剂一起，它们可用于不饱和酰胺的不对称氯环化反应，即使在环境温度和高浓度下，也可产生具有空前水平的立体选择性的产物。

  DOI：

  10.1021/ol500861z

文献信息

• A Catalytic Asymmetric Chlorocyclization of Unsaturated Amides
  作者：Arvind Jaganathan、Atefeh Garzan、Daniel C. Whitehead、Richard J. Staples、Babak Borhan

  DOI：10.1002/anie.201006910

  日期：2011.3.7

  The asymmetric chlorocyclization of unsaturated amides catalyzed by (DHQD)2PHAL yields oxazoline and dihydrooxazine derivatives (see scheme). The reaction is operationally simple and employs 1–2 mol % of the commercially available (DHQD)2PHAL (hydroquinidine 1,4‐phthalazinediyl diether) catalyst. Different substitution patterns of the olefin as well as aromatic and aliphatic olefin substituents are

  （DHQD）2 PHAL催化不饱和酰胺的不对称氯环化反应，生成恶唑啉和二氢恶嗪衍生物（参见方案）。该反应操作简单，并使用1-2 mol％的市售（DHQD）2 PHAL（氢奎尼丁1,4-萘二甲酰二醚）催化剂。烯烃以及芳族和脂族烯烃取代基的不同取代方式具有良好的耐受性。DCDPH = N，N-二氯-5,5-二苯基乙内酰脲。
• Chlorosulfonamide Salts Are Superior Electrophilic Chlorine Precursors for the Organocatalytic Asymmetric Chlorocyclization of Unsaturated Amides
  作者：Arvind Jaganathan、Babak Borhan

  DOI：10.1021/ol500861z

  日期：2014.7.18

  serve as readily available, stable, and inexpensive precursors of electrophilic chlorine in the organocatalytic asymmetric chlorofunctionalization of olefins. In conjunction with commercially available organocatalysts, they can be utilized in the asymmetric chlorocyclization of unsaturated amides to yield products with unprecedented levels of stereoselectivity even at ambient temperatures and high concentrations

  在烯烃的有机催化不对称氯官能化中，氯胺-T·3H 2 O和其他氯磺酰胺盐可作为易得，稳定且廉价的亲电子氯的前体。与可商购的有机催化剂一起，它们可用于不饱和酰胺的不对称氯环化反应，即使在环境温度和高浓度下，也可产生具有空前水平的立体选择性的产物。
• Enantioselective Bromocyclization of Allylic Amides Catalyzed by BINAP Derivatives
  作者：Yuji Kawato、Akino Kubota、Hiromi Ono、Hiromichi Egami、Yoshitaka Hamashima

  DOI：10.1021/acs.orglett.5b00220

  日期：2015.3.6

  A highly enantioselective bromocyclization of allylic amides with N-bromosuccinimide (NBS) was developed with DTBM-BINAP as a catalyst, affording chiral oxazolines with a tetrasubstituted carbon center in high yield with up to 99% ee. By utilizing the bromo substituent as a handle, the obtained compounds were converted to synthetically useful chiral building blocks.