(Z)-4-(1,3-dithian-2-yl)but-2-en-1-ol | 1197214-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: (Z)-4-(1,3-dithian-2-yl)but-2-en-1-ol
• CAS: 1197214-81-5
• 化学式: C₈H₁₄OS₂
• 分子量: 190.331
• InChiKey: UAZXOGKKYWJOOC-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-(1,3-dithian-2-yl)but-2-en-1-ol 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 [bis(trifluoroacetoxy)iodo]benzene 、 C₇H₆O₂*C₂₀H₂₇NOSi 、 叔丁基锂 、 碳酸氢钠 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 乙腈 、 三氟乙酸 、 正戊烷 为溶剂， 反应 49.5h， 生成 (-) epimyrtine
  参考文献：
  名称：

  Stereoselective Synthesis of 2,6-cis- and 2,6-trans-Piperidines through Organocatalytic Aza-Michael Reactions: A Facile Synthesis of (+)-Myrtine and (−)-Epimyrtine

  摘要：

  Both 2,6-cis- and 2,6-trans-piperidines were prepared from common substrates through organocatalytic aza-Michael reactions promoted by the gem-disubstituent effect in conjunction with dithiane coupling reactions. The organocatalytic aza-Michael reaction enabled a facile synthesis of (+)-myrtine and (-)-epimyrtine from a common substrate.

  DOI：

  10.1021/ol103064f
• 作为产物：
  描述：

  (Z)-2-((4-(1,3-dithian-2-yl)but-2-en-1-yl)oxy)tetrahydro-2H-pyran 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以1.1 g的产率得到(Z)-4-(1,3-dithian-2-yl)but-2-en-1-ol
  参考文献：
  名称：

  通过宝石二取代作用促进的串联烯丙基氧化/ Oxa-Michael反应立体选择性合成2,6-顺-四氢吡喃：（+）-新邻苯二酚内酯的合成

  摘要：

  在标题串联反应和二噻吩偶联反应的基础上，最小化使用保护基团是简洁高效地合成（+）-新邻苯二酚内酯的一大亮点（请参阅方案）。二噻吩部分的宝石二取代作用促进了烯丙基氧化后的oxa-Michael反应，以确保2,6-顺式-四氢吡喃的有效合成和高非对映选择性。

  DOI：

  10.1002/anie.200903690

文献信息

• 10.1021/acs.orglett.4c01969
  作者：Alexandridis, Anestis、Rancon, Thibault、Halliday, Abigail、Kochem, Amélie、Quintard, Adrien

  DOI：10.1021/acs.orglett.4c01969

  日期：——

  newly formed stereocenters. When iron-catalyzed borrowing hydrogen from allylic alcohols was combined with a stereocontrolled organocatalytic oxa-Michael addition, a wide array of chiral tetrahydropyrans were efficiently prepared. The reaction could be performed in a diastereoselective manner from pre-existing stereocenters or enantioselectively from achiral substrates. The key to success was the reactivity

  立体控制的 oxa-Michael 加成具有挑战性，因为该过程具有高度可逆性，最终导致新形成的立体中心外消旋化。当铁催化的烯丙醇借氢与立体控制的有机催化氧杂迈克尔加成相结合时，可以有效地制备多种手性四氢吡喃。该反应可以以非对映选择性方式从预先存在的立体中心进行或以对映选择性方式从非手性底物进行。成功的关键是铁络合物的反应活性，它对烯丙醇脱氢具有选择性，并不可逆地导致反应生成最终产物。
• Synthesis of α,α′-<i>trans</i>-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction
  作者：Megan L. Lanier、Amanda C. Kasper、Hyoungsu Kim、Jiyong Hong

  DOI：10.1021/ol500773w

  日期：2014.5.2

  Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe-Ingold) effect stereoselectively provided alpha,alpha'-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/alpha-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes.
• Stereoselective Synthesis of 2,6-<i>cis</i>-Tetrahydropyrans through a Tandem Allylic Oxidation/Oxa-Michael Reaction Promoted by the<i>gem</i>-Disubstituent Effect: Synthesis of (+)-Neopeltolide Macrolactone
  作者：Hyoungsu Kim、Yongho Park、Jiyong Hong

  DOI：10.1002/anie.200903690

  日期：2009.9.28

  protecting groups is one highlight of a concise and efficient synthesis of (+)‐neopeltolide macrolactone on the basis of the title tandem reaction and dithiane coupling reactions (see scheme). The gem‐disubstituent effect of the dithiane moiety promoted the oxa‐Michael reaction following allylic oxidation to ensure the efficient synthesis of the 2,6‐cis‐tetrahydropyran and high diastereoselectivity.

  在标题串联反应和二噻吩偶联反应的基础上，最小化使用保护基团是简洁高效地合成（+）-新邻苯二酚内酯的一大亮点（请参阅方案）。二噻吩部分的宝石二取代作用促进了烯丙基氧化后的oxa-Michael反应，以确保2,6-顺式-四氢吡喃的有效合成和高非对映选择性。
• Stereoselective Synthesis of 2,6-<i>cis</i>- and 2,6-<i>trans</i>-Piperidines through Organocatalytic Aza-Michael Reactions: A Facile Synthesis of (+)-Myrtine and (−)-Epimyrtine
  作者：Yongcheng Ying、Hyoungsu Kim、Jiyong Hong

  DOI：10.1021/ol103064f

  日期：2011.2.18

  Both 2,6-cis- and 2,6-trans-piperidines were prepared from common substrates through organocatalytic aza-Michael reactions promoted by the gem-disubstituent effect in conjunction with dithiane coupling reactions. The organocatalytic aza-Michael reaction enabled a facile synthesis of (+)-myrtine and (-)-epimyrtine from a common substrate.