(+/-)-N-(methoxycarbonyl)-3-methyl-1-phenyl-2-aminobutane | 156207-33-9

• 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: (+/-)-N-(methoxycarbonyl)-3-methyl-1-phenyl-2-aminobutane
• 英文别名: Methyl 1-benzyl-2-methylpropylcarbamate；methyl N-(3-methyl-1-phenylbutan-2-yl)carbamate
• CAS: 156207-33-9
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: QDZKBZSZMNZGFN-UHFFFAOYSA-N

物化性质

• 沸点：
  338.1±21.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-N-(methoxycarbonyl)-3-methyl-1-phenyl-2-aminobutane 在 platinum(IV) oxide 盐酸 、 PPA 、 硫酸 、 硼烷 、 氢溴酸 、 氢气 、 potassium nitrate 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0~140.0 ℃ 、344.74 kPa 条件下， 反应 5.25h， 生成 7-Bromo-3-isopropyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Exploring the active site of phenylethanolamine N-methyltransferase: 3-alkyl-7-substituted-1,2,3,4-tetrahydroisoquinoline inhibitors

  摘要：

  A series of 3 -alkyl-7 -substituted-1,2,3,4-tetrahydroisoquinolines was synthesized and these compounds were evaluated for their PNMT inhibitory potency and affinity for the (alpha(2)-adrenoceptor. 7-Nitro-, 7-bromo-, 7-aminosulfonyl-, or 7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs that possess a 3-alkyl substituent that is longer than a methyl group showed decreased PNMT inhibitory potency, except for 3-propyl-7-aminosulfonyl-THIQ, which displayed excellent PNMT inhibitory potency. The rank order for selectivity (PNMT vs the alpha(2)-adrenoceptor) is 3 -alkyl -7 -aminosulfonyl-THIQs congruent to 3-alkyl-7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs > 3-alkyl-7-nitro-THlQs > 3-alkyl-7-bromo-THIQs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.015
• 作为产物：
  描述：

  苄基氯化镁 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.5h， 生成 (+/-)-N-(methoxycarbonyl)-3-methyl-1-phenyl-2-aminobutane
  参考文献：
  名称：

  Exploring the active site of phenylethanolamine N-methyltransferase: 3-alkyl-7-substituted-1,2,3,4-tetrahydroisoquinoline inhibitors

  摘要：

  A series of 3 -alkyl-7 -substituted-1,2,3,4-tetrahydroisoquinolines was synthesized and these compounds were evaluated for their PNMT inhibitory potency and affinity for the (alpha(2)-adrenoceptor. 7-Nitro-, 7-bromo-, 7-aminosulfonyl-, or 7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs that possess a 3-alkyl substituent that is longer than a methyl group showed decreased PNMT inhibitory potency, except for 3-propyl-7-aminosulfonyl-THIQ, which displayed excellent PNMT inhibitory potency. The rank order for selectivity (PNMT vs the alpha(2)-adrenoceptor) is 3 -alkyl -7 -aminosulfonyl-THIQs congruent to 3-alkyl-7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs > 3-alkyl-7-nitro-THlQs > 3-alkyl-7-bromo-THIQs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.015

文献信息

• Reaction of N-acyl-α-methoxyamines with organozinc reagents. A convenient method for the synthesis of homoallylamines and β-amino esters
  作者：Naoki Kise、Hiroki Yamazaki、Toshirou Mabuchi、Tatsuya Shono

  DOI：10.1016/s0040-4039(00)76758-x

  日期：1994.3

  The reaction of N-acyl-alpha-methoxyamines with allyl-, propargyl-, and benzylzinc bromides and Reformatsky reagents proceeds in THF at room temperature. Homoallyl- and homopropargylamines and beta-amino esters are synthesized in good yields.
• Kise Naoki, Yamazaki Hiroki, Mabuchi Toshirou, Shono Tatsuya, Tetrahedron Lett, 35 (1994) N 10, S 1561-1564
  作者：Kise Naoki, Yamazaki Hiroki, Mabuchi Toshirou, Shono Tatsuya

  DOI：——

  日期：——
• Exploring the active site of phenylethanolamine N-methyltransferase: 3-alkyl-7-substituted-1,2,3,4-tetrahydroisoquinoline inhibitors
  作者：Gary L. Grunewald、F. Anthony Romero、Alex D. Chieu、Kelcie J. Fincham、Seema R. Bhat、Kevin R. Criscione

  DOI：10.1016/j.bmc.2004.11.015

  日期：2005.2

  A series of 3 -alkyl-7 -substituted-1,2,3,4-tetrahydroisoquinolines was synthesized and these compounds were evaluated for their PNMT inhibitory potency and affinity for the (alpha(2)-adrenoceptor. 7-Nitro-, 7-bromo-, 7-aminosulfonyl-, or 7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs that possess a 3-alkyl substituent that is longer than a methyl group showed decreased PNMT inhibitory potency, except for 3-propyl-7-aminosulfonyl-THIQ, which displayed excellent PNMT inhibitory potency. The rank order for selectivity (PNMT vs the alpha(2)-adrenoceptor) is 3 -alkyl -7 -aminosulfonyl-THIQs congruent to 3-alkyl-7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs > 3-alkyl-7-nitro-THlQs > 3-alkyl-7-bromo-THIQs. (C) 2004 Elsevier Ltd. All rights reserved.