p-isopropylbenzaldehyde N-(tert-butoxycarbonyl)imine | 1046828-42-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: p-isopropylbenzaldehyde N-(tert-butoxycarbonyl)imine
• 英文别名: tert-butyl 4-isopropylbenzylidenecarbamate
• CAS: 1046828-42-5
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: HEOLKFSZGHHRBH-UHFFFAOYSA-N

物化性质

• 沸点：
  323.1±35.0 °C(predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  p-isopropylbenzaldehyde N-(tert-butoxycarbonyl)imine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 indium 、 L-脯氨酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 30.0h， 生成 ((2R,4S,5S,6S)-2-methyl-4-hydroxy-6-(4-isopropylphenyl)-5-methylpiperidin-2-yl)acetate
  参考文献：
  名称：

  A concise diastereoselective approach to enantioenriched substituted piperidines and their in vitro cytotoxicity evaluation

  摘要：

  A library of diversely stereo-oriented, highly substituted 2,6-cis piperidine derivatives were synthesized, and evaluated for their anticancer activity in cancer cells that included A549 (lung cancer, CCL-185), MCF7 (breast cancer (HTB-22), DU145 (prostate cancer (HTB-81), and HeLa (cervical cancer, CCL-2). One stereo-variant emerged as a promising candidate for further design based structure-activity studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.003
• 作为产物：
  描述：

  4-异丙基苯甲醛 在 甲酸 、 potassium carbonate 、 sodium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 42.0h， 生成 p-isopropylbenzaldehyde N-(tert-butoxycarbonyl)imine
  参考文献：
  名称：

  Copper(I)-Catalyzed Asymmetric Pinacolboryl Addition of N-Boc-imines Using a Chiral Sulfoxide–Phosphine Ligand

  摘要：

  Highly efficient and enantioselective copper(I)-catalyzed pinacolboryl addition of N-Boc-imines is reported. By using a single chiral sulfoxide-(dialkyl)phosphine (SOP) ligand, both enantiomeric isomers of alpha-amino boronic esters were obtained through an achiral counteranion switch.

  DOI：

  10.1021/acs.orglett.5b00934

文献信息

• Enantioselective Mannich-Type Reactions to Construct Trifluoromethylthio-Containing Tetrasubstituted Carbon Stereocenters <i>via</i> Asymmetric Dual-Reagent Catalysis
  作者：Lijun Xu、Hongyu Wang、Changwu Zheng、Gang Zhao

  DOI：10.1002/adsc.201700321

  日期：2017.9.4

  stereocenters bearing both a trifluoromethylthio (SCF3) group and a cyano group has been realized, through asymmetric organophosphine-catalyzed Mannich-type reactions. The products were obtained in high yields and moderate to high enantioselectivities. Two diastereoisomers could be isolated from each reaction (overall 25 examples), rendering this approach a viable opportunity for molecular diversity generation

  通过不对称有机膦催化的曼尼希型反应，已经实现了构建同时具有三氟甲硫基（SCF 3）基团和氰基基团的四取代碳立构中心的方法。以高收率和中等至高对映选择性获得产物。可以从每个反应中分离出两个非对映异构体（总共25个实例），从而使该方法成为分子多样性产生和相关药物候选物生物活性改善的可行机会。
• Enantioselective Vinylogous Mannich‐Type Reactions to Construct CF ₃ S‐Containing Stereocenters Catalysed by Chiral Quaternary Phosphonium Salts
  作者：Lijun Xu、Longhui Yu、Jun Liu、Hongyu Wang、Changwu Zheng、Gang Zhao

  DOI：10.1002/adsc.201901621

  日期：2020.4.27

  A series of benzyl trifluoromethyl sulphides bearing a nitro group were utilized as CF3S‐containing building blocks to construct chiral CF3S‐containing molecules via enantioselective vinylogous Mannich‐type reactions. In such reactions, high yields and enantioselectivities were obtained using chiral quaternary phosphonium salts derived from amino acids. Moreover, a chiral cyclic urea bearing the CF3S

  一系列带有硝基的苄基三氟甲基硫化物被用作含CF 3 S的结构单元，通过对映选择性乙烯基类Mannich型反应构建手性CF 3 S分子。在这种反应中，使用衍生自氨基酸的手性季phospho盐可获得高产率和对映选择性。此外，从产物的进一步转化获得带有CF 3 S部分的手性环状脲。
• Chemodivergent and Stereoselective Construction of <i>gem</i>-Difluoroallylic Amines from Masked Difluorodiazo Reagents
  作者：Jun-Liang Zeng、Yue Zhang、Meng-Meng Zheng、Zhi-Qi Zhang、Xiao-Song Xue、Fa-Guang Zhang、Jun-An Ma

  DOI：10.1021/acs.orglett.9b02989

  日期：2019.10.18

  report a general and efficient approach to construct achiral and chiral gem-difluoroallylic amines from a masked difluorodiazo reagent (PhSO2CF2CHN2) and readily available imines. This facile protocol takes advantage of the phenylsulfonyl and diazo moieties as efficient activating and directing groups to assist difluoroalkyl incorporation and facilitate the chemodivergent and stereoselective formation

  我们报告了一种一般有效的方法，可以从被掩盖的二氟重氮试剂（PhSO2CF2CHN2）和现成的亚胺中构建非手性和手性的gem-difluoroallylic胺。该简便的方案利用苯磺酰基和重氮基团作为有效的活化和引导基团的优势，以协助二氟烷基的结合并促进宝石-二氟烯丙基胺的化学发散和立体选择性形成。
• Redox Economic Synthesis of TrisubstitutedPiperidones via Ruthenium Catalyzed Atom‐Economic Couplings of N‐Protected 1,5‐Aminoalcohols and Michael Acceptors
  作者：Barry M. Trost、Debayan Sarkar、Nabakumar Bera

  DOI：10.1002/adsc.201900881

  日期：2019.12.17

  An efficient atom‐economic coupling of 1,5‐amino alcohols and Michael acceptors has been developed employing [CpRu(MeCN)3]PF6 as a key catalyst to synthesize α,β‐unsaturated ketones with exclusive generation of E‐geometrical isomers at room temperature without any co‐catalyst and additives. A base catalysed 6‐endo‐trig cyclization of the α,β‐unsaturated ketone delivers a direct access to tri‐substituted

  利用[CpRu（MeCN）3 ] PF 6作为关键催化剂，开发了一种高效的1,5-氨基醇与迈克尔受体的原子-经济偶联反应，以合成α，β-不饱和酮，并在此独家生成E-几何异构体。室温，无助催化剂和添加剂。碱性催化的α，β-不饱和酮的6-内-trig环化可直接获得三取代的哌啶酮。
• Highly Efficient Catalytic Enantioselective Mannich Reaction of Malonates with<i>N</i>-<i>tert</i>-Butoxycarbonyl Imines by Using Yb(OTf)₃/Pybox Catalysts at Room Temperature
  作者：Babak Karimi、Ehsan Jafari、Dieter Enders

  DOI：10.1002/chem.201300241

  日期：2013.7.29

  Go Mannich! A highly efficient and enantioselective method for the direct asymmetric reaction of dibenzyl malonate with N‐tert‐butoxycarbonyl aldimines in the presence of Yb(OTf)3 and iPr‐pybox complexes is described (see scheme; pybox=pyridine bisoxazoline).

  去曼尼希！用于与丙二酸二苄酯的直接不对称反应中的高效率和不对称方法ñ -叔在镱的存在（OTF）丁氧羰基醛亚胺3和我描述镨pybox复合物（参见方案; pybox =吡啶二恶唑啉）。