5-(benzyloxy)-2-chloropentanal | 1377322-27-4

• 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: 5-(benzyloxy)-2-chloropentanal
• 英文别名: 2-chloro-5-phenylmethoxypentanal
• CAS: 1377322-27-4
• 化学式: C₁₂H₁₅ClO₂
• 分子量: 226.703
• InChiKey: KQDKPYCOTCAUMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-2-chloropentanal 、 (1-acetyl-2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid methyl ester 在 C₂₁H₂₂N₃O⁽¹⁺⁾*Cl^(1-) 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 methyl 9-acetyl-3-(3-(benzyloxy)propyl)-2-oxo-2,3,4,9-tetrahydropyrano[2,3-b]indole-4-carboxylate
  参考文献：
  名称：

  N-Heterocyclic Carbene (NHC)-Catalyzed Highly Diastereo- and Enantioselective Oxo-Diels–Alder Reactions for Synthesis of Fused Pyrano[2,3-b]indoles

  摘要：

  A chiral N-heterocyclic carbene (NHC)-catalyzed Diels-Alder reaction of 2-oxoindolin-3-ylidenes and alpha-chloroaldehydes was developed for the synthesis of fused pyrano[2,3-b]indoles in good to excellent yields (up to 99%) with high cis-diastereoselectivities (>99:1 dr) and enantioselectivities (up to >99% ee).

  DOI：

  10.1021/ol301175z

文献信息

• Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones
  作者：Limin Yang、Yunbo Lv、Fei Wang、Guofu Zhong

  DOI：10.1039/c8ob00925b

  日期：——

  A chiral N-heterocyclic carbene (NHC)-catalyzed 1,3-dipolar [3 + 2] cycloaddition reaction of 3-oxopyrazolidin-1-ium-2-ides and α-chloroaldehydes was developed for the synthesis of pyrazolo[1,2-a]pyrazole-1,7-diones in moderate to good yields (up to 76%) with good enantioselectivities (up to 98% ee) and diastereoselectivities (up to 8 : 1 dr).

  为了合成吡唑并[1,2]，开发了一种手性N-杂环卡宾（NHC）催化的3-氧杂吡唑烷-1-鎓-2-化物与α-氯醛的1,3-偶极[3 + 2]环加成反应。 -一个]吡唑-1,7-二酮在中度至良好的产率（高达76％）的对映选择性好（高达98％ee）和非对映选择性（高达8：1个，DR）。
• Asymmetric NHC-Catalyzed Aza-Diels–Alder Reactions: Highly Enantioselective Route to α-Amino Acid Derivatives and DFT Calculations
  作者：Limin Yang、Fei Wang、Richmond Lee、Yunbo Lv、Kuo-Wei Huang、Guofu Zhong

  DOI：10.1021/ol501424f

  日期：2014.8.1

  A facile N-heterocyclic carbene catalytic enantioselective aza-Diels–Alder reaction of oxodiazenes with α-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental

  据报道，恶二氮烯与α-氯醛作为亲二烯体前体的N-杂环卡宾催化的对映选择性氮杂-Diels-Alder反应简便，对映选择性（ee> 99％）和收率优异（高达93％）。DFT研究表明，顺式-TSa是由氧二氮烯的顶面方法转变为顺式-IIa的方式，是最有利的过渡态，与实验观察结果一致。