methyl 3-(N,N-diisopropylamino)butanoate | 119645-12-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(N,N-diisopropylamino)butanoate
• 英文别名: methyl 3-(diisopropylamino)butanoate；methyl 3-[di(propan-2-yl)amino]butanoate
• CAS: 119645-12-4
• 化学式: C₁₁H₂₃NO₂
• 分子量: 201.309
• InChiKey: UREIANFHGHFSGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(N,N-diisopropylamino)butanoate 在 lithium diisopropyl amide 作用下， 生成
  参考文献：
  名称：

  A novel synthetic approach to α-alkylidene-α-lactams

  摘要：

  DOI：

  10.1016/s0040-4039(00)97398-2
• 作为产物：
  描述：

  巴豆酸甲酯 、 二异丙胺 在 ytterbium trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 50.0 ℃ 、950.0 MPa 条件下， 反应 24.0h， 以10%的产率得到methyl 3-(N,N-diisopropylamino)butanoate
  参考文献：
  名称：

  催化高压合成受阻β-氨基酯

  摘要：

  受阻的β-氨基酯是在催化量的三氟甲磺酸presence存在下，在高压下将胺共轭加成到两个都带有大分子基团的α，β-不饱和酯上，以中等至高收率获得的。

  DOI：

  10.1016/0040-4039(94)02215-w

文献信息

• Lithium n-benzyltrimethylsilylamide (LSA): a new reagent for conjugate addition - enolate trapping reactions
  作者：Naoki Asao、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1016/s0040-4020(01)86664-3

  日期：1988.1

  4-manner, though the reaction of ordinary lithium amides with α,β-unsaturated carbonyl compounds is accompanied with a 1,2-addition and hydrogen abstraction at the γ-position. The conjugate addition via LSA followed by enolate trapping with electrophiles produces the corresponding α-substituted β-amino esters, which are, in turn, converted into β-lactams and α-substituted α, β-unsaturated esters.

  尽管普通锂酰胺与α，β-不饱和羰基化合物的反应伴随有1,2-加成和γ-氢的夺氢，但N-苄基三甲基甲硅烷基锂（LSA）可以1,4-方式添加到巴豆酸中。位置。经由LSA的共轭添加，然后用亲电试剂进行烯醇化捕集，产生相应的α-取代的β-氨基酯，其随后转化为β-内酰胺和α-取代的α，β-不饱和酯。
• Preparation of .alpha.-Methylene and .alpha.-Ethylidene .beta.-Lactams via the Ester Enolate-Imine Condensation Using .beta.-(Dialkylamino) Esters as Starting Materials: Scope and Synthetic Applications
  作者：Benito Alcaide、Gemma Esteban、Yolanda Martin-Cantalejo、Joaquin Plumet、Julian Rodriguez-Lopez、Angeles Monge、Virginia Perez-Garcia

  DOI：10.1021/jo00105a013

  日期：1994.12

  A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.
• ALCAIDE, BENITO;PLUMET, JOAQUIN;RODRIGUEZ-LIPEZ, JULIAN;SANCHEZ-CANTALEJO+, TETRAHEDRON LETT., 31,(1990) N7, C. 2493-2496
  作者：ALCAIDE, BENITO、PLUMET, JOAQUIN、RODRIGUEZ-LIPEZ, JULIAN、SANCHEZ-CANTALEJO+

  DOI：——

  日期：——
• ASAO, NAOKI;UYEHARA, TADAO;YAMAMOTO, YOSHINORI, TETRAHEDRON, 44,(1988) N 13, 4173-4180
  作者：ASAO, NAOKI、UYEHARA, TADAO、YAMAMOTO, YOSHINORI

  DOI：——

  日期：——
• A novel synthetic approach to α-alkylidene-α-lactams
  作者：Benito Alcaide、Joaquin Plumet、Julián Rodríguez-López、Yolanda M. Sánchez-Cantalejo

  DOI：10.1016/s0040-4039(00)97398-2

  日期：1990.1