N,N-bis(4-methoxyphenyl)malonamic acid tert-butyl ester | 1134365-97-1

• 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,N-bis(4-methoxyphenyl)malonamic acid tert-butyl ester
• 英文别名: N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester；tert-butyl 3-(4-methoxy-N-(4-methoxyphenyl)anilino)-3-oxopropanoate
• CAS: 1134365-97-1
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: BPWHOYICQAMKGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis(4-methoxyphenyl)malonamic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 potassium hydroxide 、 (11bS,11b’S)-2,6-bis(3,4,5-trifluorophenyl)-3,3’,5,5’-tetrahydro-4,4’-spirobi[dinaphtho[2,1-c:1’,2’-e]azepin]-4-ium bromide 作用下， 以 二丁醚 、 甲苯 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands

  摘要：

  The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.064
• 作为产物：
  描述：

  丙二酸单叔丁酯 、 4,4'-二甲氧基二苯胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N,N-bis(4-methoxyphenyl)malonamic acid tert-butyl ester
  参考文献：
  名称：

  The highly enantioselective phase-transfer catalytic mono-alkylation of malonamic esters

  摘要：

  在1摩尔%(S,S)-3,4,5-三氟苯基-NAS溴化物的存在下，N,N-二烷基丙二酰胺叔丁酯的相转移催化烷基化反应，以高度对映选择性(高达96% ee)制备了(S)-单-α-烷基化产物，这些产物可以方便地转化为多样的手性构建块，而不损失手性。

  DOI：

  10.1039/b821468a

文献信息

• The highly enantioselective phase-transfer catalytic mono-alkylation of malonamic esters
  作者：Mi-hyun Kim、Sea-hoon Choi、Yeon-Ju Lee、Jihye Lee、Keepyung Nahm、Byeong-Seon Jeong、Hyeung-geun Park、Sang-sup Jew

  DOI：10.1039/b821468a

  日期：——

  The phase-transfer catalytic alkylation of N,N-dialkylmalonamic tert-butyl esters in the presence of 1 mol% of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded highly enantioselective (S)-mono-α-alkylated products (up to 96% ee), which could be readily converted into versatile chiral building blocks without loss of chirality.

  在1摩尔%(S,S)-3,4,5-三氟苯基-NAS溴化物的存在下，N,N-二烷基丙二酰胺叔丁酯的相转移催化烷基化反应，以高度对映选择性(高达96% ee)制备了(S)-单-α-烷基化产物，这些产物可以方便地转化为多样的手性构建块，而不损失手性。
• Synthesis of (−)-Paroxetine via Enantioselective Phase-Transfer Catalytic Monoalkylation of Malonamide Ester
  作者：Mi-hyun Kim、Yohan Park、Byeong-Seon Jeong、Hyeung-geun Park、Sang-sup Jew

  DOI：10.1021/ol100928v

  日期：2010.6.18

  A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.
• Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands
  作者：Myeong Seop Kim、Yooran Ki、Song Yeon Ahn、Suyoung Yoon、Sung-Eun Kim、Hyeung-Geun Park、Wei Sun、Karam Son、Minghua Cui、Sun Choi、Larry V. Pearce、Timothy E. Esch、Ian A. DeAndrea-Lazarus、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2013.10.064

  日期：2014.1

  The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R. (C) 2013 Elsevier Ltd. All rights reserved.