cis-2-(ethenyl)tetrahydropyran-3-pl | 101208-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: cis-2-(ethenyl)tetrahydropyran-3-pl
• 英文别名: (2S,3S)-2-ethenyloxan-3-ol
• CAS: 101208-75-7；118916-98-6；118916-99-7；121422-51-3；121422-75-1
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: CDQZNJSWJFGJRQ-BQBZGAKWSA-N

物化性质

• 沸点：
  172.0±40.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-2-(ethenyl)tetrahydropyran-3-pl 、 3-溴丙烯 生成 cis-2-<3-(2-propenyloxy)tetrahydro-2H-pyran-2-yl>ethanal
  参考文献：
  名称：

  分子内烯丙基硼化反应合成顺式-二氢吡喃和三-四氢吡喃

  摘要：

  一锅步骤进行说明，其中ω氧代γ-alkoxyallylboronates 8从ω烯丙氧基-醛生成9和环化成顺式-双取代的vinyltetrahydropyranols 4。重复此程序对烯丙氧基醛11导致顺式-顺式-顺式-二-四氢吡喃醇12，并导致顺式-顺式-顺式-顺式-顺式-三四环戊醇15。

  DOI：

  10.1016/0040-4039(95)00013-3
• 作为产物：
  描述：

  4-allyloxybutanal 生成 cis-2-(ethenyl)tetrahydropyran-3-pl
  参考文献：
  名称：

  分子内烯丙基硼化反应合成顺式-二氢吡喃和三-四氢吡喃

  摘要：

  一锅步骤进行说明，其中ω氧代γ-alkoxyallylboronates 8从ω烯丙氧基-醛生成9和环化成顺式-双取代的vinyltetrahydropyranols 4。重复此程序对烯丙氧基醛11导致顺式-顺式-顺式-二-四氢吡喃醇12，并导致顺式-顺式-顺式-顺式-顺式-三四环戊醇15。

  DOI：

  10.1016/0040-4039(95)00013-3

文献信息

• Intramolecular allylboration of γ-(ω-formylalkoxy)allylboronates for syntheses of trans- or cis-2-(ethenyl)tetrahydropyran-3-ol and 2-(ethenyl)oxepan-3-ol
  作者：Yasunori Yamamoto、Kazunori Kurihara、Akihiko Yamada、Miki Takahashi、Youichi Takahashi、Norio Miyaura

  DOI：10.1016/s0040-4020(02)01557-0

  日期：2003.1

  give 3-alkoxy-1-alkenylboronates 5. The latter gave (E)-3-alkoxyallylboronates (8: (E)-(MeO)2CHCH2(CH2)nCH2OCHCHCH2Bpin, n=1–3) when they were subjected to iridium-catalyzed isomerization of the double bond. The corresponding (Z)-isomers 10 were synthesized by nickel-catalyzed isomerization of 5. Both allylboronates underwent intramolecular allylboration leading to the formation of trans-2-(ethen

  将3-烷氧基-1-炔烃4与频哪醇硼烷（HBpin）氢硼化，得到3-烷氧基-1-烯基硼酸酯5。后者在铱催化下生成（E）-3-烷氧基烯丙基硼酸酯（8：（E）-（MeO）2 CHCH 2（CH 2）n CH 2 OCH = CHCH 2 Bpin，n = 1–3）。双键的异构化。通过镍催化的5的异构化合成相应的（Z）异构体10。两种烯丙基硼酸酯都经历了分子内烯丙基硼化作用，导致形成反式-2-（乙烯基）四氢吡喃-3-醇或2-（乙烯基）从oxepan -3-醇8和相应的顺从异构体10中的Yb（OTF）的存在3（20摩尔％）在乙腈水溶液中在90°C下。
• Stereoselective Synthesis of Alcohols, L. Synthesis and Conformational Studies of 1,5-Dioxa-cis-decalin
  作者：Reinhard W. Hoffmann、Ingo Münster

  DOI：10.1002/jlac.199719970614

  日期：1997.6

  cis-2-Vinyltetrahydropyran-3-ol (6) is accessible by a selective intramolecular allylboration reaction. Compound 6 was converted into 1,4-dioxa-cis-decaline (4) and cis-syn-cis-perhydrotrioxaanthracene 32; heterocycles with fused tetrahydropyran rings. These ring systems populate predominantly the conformation in which the oxygen atoms are in a gauche arrangement. The tricycle 31 is a rigid derivative

  顺式-2-乙烯基四氢吡喃-3-醇（6）可通过选择性分子内烯丙基硼化反应获得。化合物6转化成1,4-二氧杂-顺式-decaline（4）和顺式-顺式-perhydrotrioxaanthracene 32 ; 稠合四氢吡喃环的杂环。这些环系统主要构成氧原子呈薄纱状排列的构象。三轮车31是14-冠-3的刚性衍生物，并且与12-冠-3的情况一样，它与乙腈中的锂离子形成络合物。
• Intramolecular Reaction of (γ-Alkoxyallyl)stannane with Aldehyde:  Origin of the Stereoselectivities
  作者：Isao Kadota、Miho Kawada、Vladimir Gevorgyan、Yoshinori Yamamoto

  DOI：10.1021/jo971309c

  日期：1997.10.1

  The intramolecular cyclization of simple acyclic (gamma-alkoxyallyl)stannane aldehydes 1, 2, and 12-15 was investigated to elucidate the relationship between the geometry of the double bond of the allylstannanes, the ring size of cyclic ethers produced by the cyclization, and the procedures for promoting the cyclization. The Lewis acid-mediated cyclization of 1-2, 12-13, and 14-15 gave the trans cyclic ethers 3, 39, and 41, respectively, either predominantly or exclusively irrespective of the geometry of the double bond and of the ring size of the cyclic ethers. The relationship in the thermal cyclization of 1 and 2, which gave the 6-membered cyclic ethers 4 and 3, was straightforward; the Z isomer 1 gave the cis product 4, and the E isomer 2 afforded the trans product 3. However, the relationship in the thermal cyclization of 12 and 13 which afforded the 5-membered cyclic ethers 39 and 40 was different from that expected from the cyclization via the well-accepted cyclic transition state, as observed in the case of 1 and 2. Both the Z (12) and E (13) isomers gave the cis cyclic ether 40 either predominantly or exclusively. The protic acid-mediated (or-catalyzed) cyclization of 12-13 and 14-15 gave the trans cyclic ethers 39 and 41, respectively, regardless of the geometry of the double bonds. On the other hand, the protic acid-promoted cyclization of 1 and 2 was very strange; the Z isomer 1 gave the cis isomer 4, and the E isomer 2 afforded the trans isomer 3. The mechanisms for these cyclization reactions are proposed.
• Activation of 6-endo over 5-exo hydroxy epoxide openings. Stereoselective and ring selective synthesis of tetrahydrofuran and tetrahydropyran systems
  作者：K. C. Nicolaou、C. V. C. Prasad、P. K. Somers、C. K. Hwang

  DOI：10.1021/ja00196a043

  日期：1989.7
• Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation
  作者：Vladimir Gevorgyan、Isao Kadota、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(00)91783-0

  日期：1993.2

  Bronsted acid catalyzed or Bu4NF-TiCl4 mediated cyclization of (Z)-omega-stannyl ether aldehyde 1a gives 2a, whereas (E)-isomer 1b affords 2b. To explain this stereochemical outcome, a push-pull mechanism is proposed.