5-(Benzyloxy)-2-(chloromethyl)-1,3-dimethylbenzene | 1416989-94-0

• 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-(chloromethyl)-1,3-dimethylbenzene
• 英文别名: 2-(chloromethyl)-1,3-dimethyl-5-phenylmethoxybenzene
• CAS: 1416989-94-0
• 化学式: C₁₆H₁₇ClO
• 分子量: 260.763
• InChiKey: WFORXHHZSDLDFC-UHFFFAOYSA-N

物化性质

• 沸点：
  396.0±37.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-[(S)-叔丁基亚磺酰基]亚氨基乙酸乙酯 、 5-(Benzyloxy)-2-(chloromethyl)-1,3-dimethylbenzene 在 magnesium 、 lithium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以70%的产率得到ethyl (2S)-2-[[(S)-tert-butylsulfinyl]amino]-3-(2,6-dimethyl-4-phenylmethoxyphenyl)propanoate
  参考文献：
  名称：

  Unnatural Chiral N-tert-Butanesulfinyl α-Amino Acid Synthesis; A General Synthetic Strategy to N-Boc-Phenylalanine Analogue Alternatives

  摘要：

  This work provides a general approach to unnatural chiral N-tert-butanesulfinyl alpha-amino acid synthesis with high yields and excellent diastereoselectivities (dr up to 98: 2). The asymmetric addition of organometallic reagents to N-tert-butylsulfinyl imino acetate proceeded with excellent diastereo- and regioselectivities even on a 10 mmol scale. The sterically constrained 2',6'-dimethyltyrosine (Dmt) derivative was also readily prepared from commercially available and inexpensive starting materials through simple steps.

  DOI：

  10.1055/s-0032-1317298
• 作为产物：
  描述：

  4-苄氧基-2,6-二甲基苯甲醛 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 5-(Benzyloxy)-2-(chloromethyl)-1,3-dimethylbenzene
  参考文献：
  名称：

  Unnatural Chiral N-tert-Butanesulfinyl α-Amino Acid Synthesis; A General Synthetic Strategy to N-Boc-Phenylalanine Analogue Alternatives

  摘要：

  This work provides a general approach to unnatural chiral N-tert-butanesulfinyl alpha-amino acid synthesis with high yields and excellent diastereoselectivities (dr up to 98: 2). The asymmetric addition of organometallic reagents to N-tert-butylsulfinyl imino acetate proceeded with excellent diastereo- and regioselectivities even on a 10 mmol scale. The sterically constrained 2',6'-dimethyltyrosine (Dmt) derivative was also readily prepared from commercially available and inexpensive starting materials through simple steps.

  DOI：

  10.1055/s-0032-1317298