1-[(1R,2R)-2-aminocyclohexyl]-3-[3-[[27-[3-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea | 1426836-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(1R,2R)-2-aminocyclohexyl]-3-[3-[[27-[3-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea
• CAS: 1426836-12-5
• 化学式: C₆₄H₉₄N₆O₄S₂
• 分子量: 1075.62
• InChiKey: AOODCOGVKFMZII-DOLHKDQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  76
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  223
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[(1R,2R)-2-aminocyclohexyl]-3-[3-[[27-[3-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea 、 丙醛 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 24.25h， 以75%的产率得到25,27-bis(3-(2-dipropylaminocyclohexyl)thiourea)-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene
  参考文献：
  名称：

  新型高效双功能杯芳烃硫脲衍生物作为硝基烯烃与二酮对映选择性迈克尔反应的有机催化剂

  摘要：

  合成了新的双功能杯芳烃硫脲有机催化剂，并应用于室温下乙酰丙酮与各种硝基烯烃的催化不对称迈克尔加成反应。相应的加合物以良好到极好的收率获得，具有极好的对映选择性（高达 92% ee）。本研究证明了将两种立体控制结构结合到单一催化剂中的优势。值得注意的是，它为手性有机分子的催化不对称合成提供了一种简单方便的双立体控制方法。

  DOI：

  10.1007/s10847-017-0761-1
• 作为产物：
  描述：

  1,1'-(((15,35,55,75-tetra-tert-butyl-32,72-dihydroxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,52-diyl)bis(oxy))bis(propane-3,1-diyl))bis(3-((1R,2R)-2-(1,3-dioxoisoindolin-2-yl)cyclohexyl)thiourea) 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以84%的产率得到1-[(1R,2R)-2-aminocyclohexyl]-3-[3-[[27-[3-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea
  参考文献：
  名称：

  基于杯芳烃的高效伯胺-硫脲有机催化剂用于醛与硝基苯乙烯的不对称迈克尔加成

  摘要：

  首次描述了从对叔丁基杯[4]芳烃合成基于杯[4]芳烃的手性双功能伯胺-硫脲催化剂。杯[4]芳烃基催化剂被成功应用于促进醛与硝基烯烃的迈克尔加成，优先提供（R）-或（S）-加合物的高产率（高达95%）和优异的对映选择性（高达99%） es）。

  DOI：

  10.1080/10610278.2013.773331
• 作为试剂：
  描述：

  N-苯基马来酰亚胺 、 2-甲基戊醛 在 1-[(1R,2R)-2-aminocyclohexyl]-3-[3-[[27-[3-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到(R)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpentanal
  参考文献：
  名称：

  Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides

  摘要：

  Calix[4]arene based chiral bifunctional thiourea-primary amines have been shown to act as effective catalysts for the Michael addition of aldehydes to maleimides for the first time. The corresponding adducts were generally obtained preferentially in (R)- or (S)-forms with high yields (up to 99%) and with high to excellent enantioselectivities (up to 98% ee). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.010

文献信息

• Calixarene-derived chiral tertiary amine–thiourea organocatalyzed asymmetric Michael additions of acetyl acetone and dimethyl malonate to nitroolefins
  作者：Mustafa Durmaz、Aysun Tataroglu、Horu Yilmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2016.01.004

  日期：2016.2

  Novel bifunctional chiral thiourea-tertiary amines bearing a calix[4]arene scaffold were synthesized and applied in catalytic asymmetric Michael addition of acetyl acetone and dimethyl malonate to nitroolefins. The corresponding adducts were obtained in excellent yields (up to 99%) and with high enantioselectivities (up to 94% ee). (C) 2016 Elsevier Ltd. All rights reserved.
• Novel efficient bifunctional calixarene thiourea organocatalysts: synthesis and application in the direct enantioselective aldol reactions
  作者：Hayriye Nevin Genc、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2016.01.011

  日期：2016.3

  Novel efficient bifunctional calixarene thiourea organocatalysts have been designed as efficient organocatalysts for direct asymmetric aldol reactions between acetone and aromatic aldehydes. The reactions generated the corresponding products in satisfactory isolated yields (up to 96%) and with excellent enantiomeric excesses (up to 99%) in the presence of catalyst (10 mol %). (C) 2016 Elsevier Ltd. All rights reserved.
• Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides
  作者：Mustafa Durmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2013.09.010

  日期：2013.12

  Calix[4]arene based chiral bifunctional thiourea-primary amines have been shown to act as effective catalysts for the Michael addition of aldehydes to maleimides for the first time. The corresponding adducts were generally obtained preferentially in (R)- or (S)-forms with high yields (up to 99%) and with high to excellent enantioselectivities (up to 98% ee). (C) 2013 Elsevier Ltd. All rights reserved.
• Novel and highly efficient bifunctional calixarene thiourea derivatives as organocatalysts for enantioselective Michael reaction of nitroolefins with diketones
  作者：Hayriye Nevin Genc、Abdulkadir Sirit

  DOI：10.1007/s10847-017-0761-1

  日期：2018.2

  New bifunctional calixarene thiourea organocatalysts were synthesized and applied in catalytic asymmetric Michael addition of acetylacetone to various nitroolefins at room temperature. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 92% ee). The present research demonstrates the advantages of incorporating two stereocontrolling structures

  合成了新的双功能杯芳烃硫脲有机催化剂，并应用于室温下乙酰丙酮与各种硝基烯烃的催化不对称迈克尔加成反应。相应的加合物以良好到极好的收率获得，具有极好的对映选择性（高达 92% ee）。本研究证明了将两种立体控制结构结合到单一催化剂中的优势。值得注意的是，它为手性有机分子的催化不对称合成提供了一种简单方便的双立体控制方法。
• Calixarene-based highly efficient primary amine–thiourea organocatalysts for asymmetric Michael addition of aldehydes to nitrostyrenes
  作者：Mustafa Durmaz、Abdulkadir Sirit

  DOI：10.1080/10610278.2013.773331

  日期：2013.5.1

  The synthesis of calix[4]arene-based chiral bifunctional primary amine–thiourea catalysts has been described from p-tert-butylcalix[4]arene for the first time. The calix[4]arene-based catalysts were successfully applied to promote Michael addition of aldehydes with nitroalkenes affording preferentially the (R)- or (S)-adducts in high yields (up to 95%) and excellent enantioselectivities (up to 99%

  首次描述了从对叔丁基杯[4]芳烃合成基于杯[4]芳烃的手性双功能伯胺-硫脲催化剂。杯[4]芳烃基催化剂被成功应用于促进醛与硝基烯烃的迈克尔加成，优先提供（R）-或（S）-加合物的高产率（高达95%）和优异的对映选择性（高达99%） es）。