(S)-2-methyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-ol | 1318244-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-methyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-ol
• 英文别名: (3S)-2-methyl-7-tri(propan-2-yl)silylhepta-4,6-diyn-3-ol
• CAS: 1318244-99-3
• 化学式: C₁₇H₃₀OSi
• 分子量: 278.51
• InChiKey: KAXNCJSEVRDSOZ-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (3S)-2-methylhepta-4,6-diyn-3-ol
  参考文献：
  名称：

  Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes

  摘要：

  The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to alpha-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.

  DOI：

  10.1021/jo2008719
• 作为产物：
  描述：

  triisopropyl((trimethylsilyl)buta-1,3-diyn-1-yl)silane 在 甲醇 、 N-甲基麻黄碱 、 zinc trifluoromethanesulfonate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 40.33h， 生成 (S)-2-methyl-7-(triisopropylsilyl)hepta-4,6-diyn-3-ol
  参考文献：
  名称：

  Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes

  摘要：

  The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to alpha-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.

  DOI：

  10.1021/jo2008719

文献信息

• Synthesis and Biological Evaluation of Falcarinol-Type Analogues as Potential Calcium Channel Blockers
  作者：Yang Li、Wan-Li Tan、Kai Guo、Xiao-Wei Gao、Jun Wei、Dong Yi、Chun Zhang、Qin Wang

  DOI：10.1021/acs.jnatprod.1c00136

  日期：2021.8.27

  channel-blocking activity, as recorded using a manual patch clamp technique on HEK-293 cells stably expressing hCav1.2 (α1C/β2a/α2δ1). These findings suggest that the mechanism of the L-type calcium channel-blocking activity of falcarinol (1a) and its analogue (R)-2i might be involved in neuroprotection by falcarinol-type analogues by inhibiting calcium overload in the upstream of the signaling pathway.

  使用基于手性 1,1'-联萘-2-醇 (BINOL) 的催化系统合成了一系列镰刀菌醇类似物 ( 2 )的对映异构体。研究了镰刀菌素 ( 1a ) 及其类似物 ( 2 ) 对叠氮化钠 (NaN 3 )损伤的 PC12 细胞的神经保护作用。研究了结构-功能关系和可能的机制。在加入 NaN 3并在 CO 2 中培养后，用镰刀菌素类似物 ( R )- 2d和 ( R )- 2i预处理 PC12 细胞1 小时培养 24 小时导致细胞活力显着提高，如 CCK-8 测定和 Hoechst 染色所确定，与 LDH 释放和 MDA 含量减少、SOD 活性增加和 ROS 应激降低相比，与天然镰刀菌素 ( 1a )。这些观察结果表明，镰刀菌素类似物 ( R )- 2d和 ( R )- 2i可以通过增加对氧化应激的抵抗力来保护 PC12 细胞免受 NaN 3诱导的细胞凋亡。第一次，falcarinol ( 1a )
• Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes
  作者：Erin R. Graham、Rik R. Tykwinski

  DOI：10.1021/jo2008719

  日期：2011.8.19

  The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to alpha-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.