3-(3-甲氧基-4-苄氧基苯基)丙醛 | 69172-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(3-甲氧基-4-苄氧基苯基)丙醛
• 英文名称: 3-(4'-benzyloxy-3'-methoxyphenyl)propanal
• 英文别名: 3-(3-methoxy-4-benzyloxyphenyl)propionaldehyde；3-(4-(Benzyloxy)-3-methoxyphenyl)propanal；3-(3-methoxy-4-phenylmethoxyphenyl)propanal
• CAS: 69172-20-9
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: DZSWBLCQPVAVEC-UHFFFAOYSA-N

物化性质

• 沸点：
  398.8±32.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-甲氧基-4-苄氧基苯基)丙醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (+)(6S)-10-(4-Hydroxy-3-methoxyhenyl)-8,8-(1,3-propanediyldithio)-6-hydroxy-1-<(tert-butyldiphenylsilyl)oxy>decane
  参考文献：
  名称：

  Total synthesis of natural gingerols, the three active principles of ginger

  摘要：

  Natural gingerols, (+)(S)[6]-, (+)(S)[8]-, and (+)(S)[10]-gingerols, the three active principles of ginger, have been prepared from a common optically active intermediate 9 which was readily made by asymmetric synthesis from a chiral beta-keto sulfoxide 5.

  DOI：

  10.1021/jo00060a038
• 作为产物：
  描述：

  3-(4-羟基-3-甲氧基苯基)丙酸 在 吡啶 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-(3-甲氧基-4-苄氧基苯基)丙醛
  参考文献：
  名称：

  Total synthesis of natural gingerols, the three active principles of ginger

  摘要：

  Natural gingerols, (+)(S)[6]-, (+)(S)[8]-, and (+)(S)[10]-gingerols, the three active principles of ginger, have been prepared from a common optically active intermediate 9 which was readily made by asymmetric synthesis from a chiral beta-keto sulfoxide 5.

  DOI：

  10.1021/jo00060a038

文献信息

• Mevalonolactone derivatives
  申请人：Sankyo Company Limited

  公开号：US04198425A1

  公开（公告）日：1980-04-15

  This invention concerns novel mevalonolactone derivatives having the formula ##STR1## wherein A represents a direct linkage, methylene, ethylene, trimethylene or vinylene group; R.sup.1 represents hydrogen atom, or an aliphatic acyl group, benzoyl group, or a benzoyl group substituted with hydroxy, lower alkoxy, aliphatic acyloxy or halogen; R.sup.2 represents hydrogen atom, a halogen atom or methyl group; and R.sup.3, R.sup.4 and R.sup.5 are same or different and each represents hydrogen atom, a halogen atom, a lower alkyl group with or without halogen as the substituent, phenyl group, or a phenyl group substituted with halogen, lower alkoxy, aliphatic acyloxy or lower alkyl with or without halogen, or a group represented by the formula R.sup.6 O-- (in the formula, R.sup.6 means hydrogen atom, an aliphatic acyl group, benzoyl group, phenyl group, a phenylalkyl group, cinnamyl group, or a group of benzoyl, phenyl, phenylalkyl or cinnamyl in all of which the aromatic ring is substituted with hydroxy, halogen, lower alkoxy, aliphatic acyloxy or lower alkyl with or without halogen as the substituent, or a lower alkyl group with or without halogen as the substituent). The compounds are useful for the treatment of hyperlipidemia. They may be prepared by halo-lactonizing the corresponding .gamma.,.delta.-unsaturated carboxylic acid derivatives and optionally dehalogenating the resulting product, or lactonizing the corresponding .delta.-hydroxy-carboxylic acid derivatives.

  这项发明涉及具有以下结构的新型麦瓦酮内酯衍生物：其中A代表直链，亚甲基，乙烯基，三亚甲基或乙烯基；R.sup.1代表氢原子，或脂肪酰基，苯甲酰基，或苯甲酰基上带有羟基，较低的烷氧基，脂肪酰氧基或卤素基；R.sup.2代表氢原子，卤素原子或甲基基团；R.sup.3，R.sup.4和R.sup.5相同或不同，每个代表氢原子，卤素原子，带或不带卤素作为取代基的较低烷基，苯基，或带卤素，较低烷氧基，脂肪酰氧基或较低烷基，带或不带卤素的苯基，或由以下式表示的基团R.sup.6 O--（在该式中，R.sup.6代表氢原子，脂肪酰基，苯甲酰基，苯基，苯基烷基，肉桂酰基，或苯甲酰，苯基，苯基烷基或肉桂酰基的基团，其中芳香环被羟基，卤素，较低烷氧基，脂肪酰氧基或较低烷基取代或带或不带卤素作为取代基，或带或不带卤素的较低烷基）。这些化合物对治疗高脂血症有用。它们可以通过卤代内酯化相应的γ，δ-不饱和羧酸衍生物并可选择性地去卤生成的产物，或内酯化相应的δ-羟基-羧酸衍生物来制备。
• A Natural Product Inspired Tetrahydropyran Collection Yields Mitosis Modulators that Synergistically Target CSE1L and Tubulin
  作者：Tobias Voigt、Claas Gerding-Reimers、Tuyen Thi Ngoc Tran、Sabrina Bergmann、Hugo Lachance、Beate Schölermann、Andreas Brockmeyer、Petra Janning、Slava Ziegler、Herbert Waldmann

  DOI：10.1002/anie.201205728

  日期：2013.1.2

  the key step in the synthesis of tetrahydropyran derivatives. A phenotypic screen led to the identification of compounds that inhibit mitosis (as seen by the accumulation of round cells with condensed DNA and membrane blebs; see picture). These compounds were termed tubulexins as they target the CSE1L protein and the vinca alkaloid binding site of tubulin.

  聚合物结合的醛与均丙醇之间的Prins环化反应是合成四氢吡喃衍生物的关键步骤。通过对表型的筛选，可以鉴定出抑制有丝分裂的化合物（如带有浓缩DNA和膜泡的圆形细胞的积累所见；见图）。这些化合物被称为微管毒素，因为它们靶向CSE1L蛋白和微管蛋白的长春花生物碱结合位点。
• Mevalonolactone derivatives as inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase.
  作者：AIYA SATO、HIROSHI NOGUCHI、SEIJI MITSUI、ISAO KANEKO、YOKO SHIMADA

  DOI：10.1248/cpb.28.1509

  日期：——

  Mevalonolactone derivatives were prepared via stereo-and regioselective bromolactonization of γ, δ-unsaturated acids and their structure-activity relationship in connection with their inhibitory activity in vitro against 3-hydroxy-3-methylglutaryl coenzyme A (HMG CoA) reductase, a rate-limiting enzyme in cholesterol biosynthesis, was investigated.

  通过对γ, δ-不饱和酸进行立体选择性和区域选择性的溴内酯化反应制备了美瓦龙内酯衍生物，并研究了它们在体外对3-羟基-3-甲基谷氨酰辅酶A（HMG CoA）还原酶的抑制活性与其结构-活性关系，该酶是胆固醇生物合成中的限速酶。
• Enantioselective Total Synthesis of Ligraminol D and Ligraminol E
  作者：Baliram B. Mane、D. D. Kumbhar、Suresh B. Waghmode

  DOI：10.1055/s-0039-1690249

  日期：2019.12

  As a part of our ongoing research on the synthesis of bioactive constituents or molecules by using an organocatalytic approach, enantioselective total syntheses of ligraminol D and ligraminol E were achieved starting from a commercially available nonchiral aldehyde. Key steps in this synthesis were an asymmetric α-aminoxylation of an aldehyde and a Mitsunobu reaction.

  作为我们正在进行的使用有机催化方法合成生物活性成分或分子的研究的一部分，从市售的非手性醛开始实现了 ligraminol D 和 ligraminol E 的对映选择性全合成。该合成的关键步骤是醛的不对称 α-氨氧基化和光信反应。
• First total synthesis and reassignment of absolute configuration of diosniponol A and B
  作者：J.S. Yadav、Vinay K. Singh、B. Thirupathaiah、A. Bal Reddy

  DOI：10.1016/j.tetlet.2014.04.065

  日期：2014.8

  Enantioselective first total synthesis of diosniponol A and B has been achieved starting from commercially available vanillin. Wittig reaction, Keck allylation, and Prins cyclization reactions are the key steps involved in the target synthesis.

  从市售的香兰素开始已经完成了对地西酚A和B的对映选择性的第一全合成。Wittig反应，Keck烯丙基化和Prins环化反应是目标合成中涉及的关键步骤。