cis-(6-((benzyloxy)methyl)cyclohex-3-en-1-yl)methanol | 154728-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-(6-((benzyloxy)methyl)cyclohex-3-en-1-yl)methanol
• 英文别名: {(1R,6S)-6-[(Benzyloxy)methyl]cyclohex-3-en-1-yl}methanol；[(1R,6S)-6-(phenylmethoxymethyl)cyclohex-3-en-1-yl]methanol
• CAS: 154728-60-6
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: SHFMMKJBVVYUMD-LSDHHAIUSA-N

物化性质

• 沸点：
  339.7±17.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-(6-((benzyloxy)methyl)cyclohex-3-en-1-yl)methanol 在 jones' reagent 、 乙酰氯 作用下， 以 丙酮 为溶剂， 生成 methyl (1R,6S)-6-(benzyloxymethyl)cyclohex-3-enecarboxylate
  参考文献：
  名称：

  The First Synthesis of the ABC-Ring System of ‘Upenamide

  摘要：

  The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.

  DOI：

  10.1021/ol701772d
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.25h， 生成 cis-(6-((benzyloxy)methyl)cyclohex-3-en-1-yl)methanol
  参考文献：
  名称：

  通过协同烯胺、光氧化还原和钴三重催化合成芳香醛的去饱和方法

  摘要：

  协同烯胺、光氧化还原和钴三重催化为芳香醛的制备提供了一种去饱和方法。

  DOI：

  10.1002/anie.202201870

文献信息

• Synthesis of 9,11-dideoxy-9a-homoprostaglandins
  作者：T.A. Eggelte、H. de Koning、H.O. Huisman

  DOI：10.1002/recl.19770961008

  日期：——

  The synthesis of three 9,11-dideoxyprostaglandins in which the cyclopentane moiety is replaced by a six-membered ring, is described. Starting from phthalaldehydic acid (1) the aromatic PG-analogue, 7-[2-(3-hydroxy-(E)-1-octenyl)phenyl]heptanoic acid (9), was prepared in 7 steps in 49% overall yield. The cis-substituted cyclohexane PG-analogue, ethyl 7-[cis-2-(3-hydroxy-(E)-1-octenyl)cyclohexyl]heptanoate

  描述了三个9,11-二脱氧前列腺素的合成，其中环戊烷部分被六元环取代。从邻苯二酸（1）开始，以7步制备芳族PG-类似物7- [2-（3-羟基-（（E）-1-辛烯基）苯基]庚酸（9），总产率为49％。该顺式-取代的环己烷PG-类似物，7-〔顺-2-（3-羟基- （ë）-1-辛烯基）环己基]庚酸甲酯（34），在7个步骤由相同的获得53％的总收率起始原料1。的反式-取代的环己烷PG-类似物，乙基7- [反式-2-（3-羟基- （É由9-氰基-（E）-2-壬烯酸甲酯（12）以8个步骤合成）-1-辛烯基）环己基]庚酸酯（20），产率为34％。
• Stereocontrolled synthesis of functionalised cyclohexanes via the lithium amide-mediated rearrangement of a meso 4,5-disubstituted cyclohexene oxide
  作者：Peter O'Brien、Jérôme J. Tournayre

  DOI：10.1016/s0040-4020(97)10201-0

  日期：1997.12

  Reaction of a 90:10 mixture of diastereomeric meso 4,5-disubstituted cyclohexene oxides (prepared via a stereoselective epoxidation reaction) with a mixed base system of a lithium amide and potassium tert-butoxide produces a 72% yield of an allylic alcohol and a 9.6% yield of recovered epoxide, both as single diastereoisomers. The relative stereochemistry of the epoxides and the allylic alcohol is

  非对映异构的内消旋4,5-二取代的环己烯氧化物的90:10混合物（通过立体选择性环氧化反应制备）与酰胺化锂和叔丁醇钾的混合碱体系反应，可制得72％的烯丙醇和均为单一非对映异构体，回收的环氧化物的收率为9.6％。环氧化合物和烯丙基醇的相对立体化学是通过将烯丙基醇转化为新型双环醚而建立的。烯丙醇还用于制备一系列官能化的环己烷的单一非对映异构体。
• Prostaglandins
  申请人：National Research Development Corporation

  公开号：US04945106A1

  公开（公告）日：1990-07-31

  Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.

  已经制备出在血栓素受体位点表现出活性的前列腺素类似物。
• Thromboxane receptor active analogues based on the 6-oxabicyclo[3.2.1]octane ring system
  作者：G Muir、RL Jones、SG Will、T Winwick、V Peesapati、NH Wilson、N Griffiths、WV Nicholson、P Taylor、L Sawyer、AJ Blake

  DOI：10.1016/0223-5234(93)90092-s

  日期：1993.1

  Prostanoid analogues with a 6-oxabicyclo[3.2.1]octane ring and 3 different types of omega-chain have been synthesized and evaluated for biological activity on thromboxane A2 (TXA2) receptors and prostaglandin I2 (PGI2) receptors. The standard omega-chain analogue 34b is a TXA2 receptor agonist approximately 10-fold less potent than U46619 3, the standard agonist. The O-diphenyl-methyloximino-omega'-chain analogue 32 gives a PGI2-like agonist almost-equal-to 5-fold less active than EP 157, the most active molecule in this class. Conversely, 4-arylsemicarbazone omega-chain analogues 35a and 35b show TXA2 antagonism comparable to that obtained with bicyclo[2.2.2]octane and bicyclo[2.2. 1]heptane systems containing this type of omega-chain (eg EP 092).
• Prostaglandin intermediates
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0111955B1

  公开（公告）日：1986-09-17